Recent Advances in Catalytic Enantioselective Synthesis of α-Chiral Tertiary Azides★

doi:10.6023/A23070359

Acta Chimica Sinica ›› 2023, Vol. 81 ›› Issue (11): 1590-1608.DOI: 10.6023/A23070359 Previous Articles Next Articles

Special Issue: 庆祝《化学学报》创刊90周年合辑

Review

α-手性三级叠氮化合物的不对称催化合成新进展^★

高杨^a, 张学鑫^a, 余金生^a^,^*(), 周剑^a^,^b^,^c^,^*()

a 华东师范大学化学与分子工程学院石油化工分子转化与反应工程全国重点实验室上海分子治疗与新药创制工程技术研究中心上海市绿色化学与化工过程绿色化重点实验室上海 200062
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032
c 海南师范大学热带药用资源化学教育部重点实验室海口 571127

投稿日期:2023-07-28 发布日期:2023-09-30

作者简介:

高杨, 女, 汉族, 1996年出生于甘肃金昌. 2016年9月本科毕业于河西学院, 2019年9月硕士毕业于云南民族大学有机化学专业, 随后加入华东师范大学周剑教授课题组攻读博士学位, 研究方向为有机小分子催化构建α-手性三级叠氮化合物.

张学鑫, 男, 汉族, 1992年出生于甘肃张掖. 2016年9月本科毕业于河西学院, 2019年9月硕士毕业于云南民族大学有机化学专业, 随后加入华东师范大学周剑教授课题组攻读博士学位, 研究方向为手性有机硅化合物的合成.

余金生, 华东师范大学化学与分子工程学院教授, 博士生导师. 2011年本科毕业于江西师范大学; 2016年博士毕业于华东师范大学, 导师周剑教授; 2017至2019年获JSPS资助在日本微生物化学研究所从事博士后研究, 导师Masakatsu Shibasaki教授. 2019年2月加入华东师范大学开展研究工作, 主要从事有机氟硅化学和绿色农药创制等研究.

周剑, 华东师范大学化学与分子工程学院教授, 博士生导师. 本科毕业于四川师范大学; 2004年毕业于中科院上海有机所, 获理学博士学位, 导师唐勇研究员; 先后在日本东京大学Shu Kobayashi和德国马普煤炭研究所Benjamin List课题组从事博士后研究后, 于2008年底加入华东师范大学. 研究兴趣在于立足协同催化的理念, 结合新催化剂和新试剂的设计开发, 发展导向具有手性季碳的药物优势骨架的不对称催化构建新方法.

^★庆祝《化学学报》创刊90周年.

基金资助:
国家自然科学基金(21971067); 国家自然科学基金(22171087); 上海市教育委员会科研创新计划(2023ZKZD37); 上海市科技创新行动计划(20JC1416900); 上海市科技创新行动计划(21N41900500)

Recent Advances in Catalytic Enantioselective Synthesis of α-Chiral Tertiary Azides^★

Yang Gao^a, Xuexin Zhang^a, Jinsheng Yu^a(), Jian Zhou^a^,^b^,^c()

a State Key Laboratory of Molecular & Process Engineering, Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
c Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou 571127

Received:2023-07-28 Published:2023-09-30
Contact: *E-mail: jsyu@chem.ecnu.edu.cn; jzhou@chem.ecnu.edu.cn
About author:
^★Dedicated to the 90th anniversary of Acta Chimica Sinica.
Supported by:
National Natural Science Foundation of China(21971067); National Natural Science Foundation of China(22171087); Innovation Program of Shanghai Municipal Education Commission(2023ZKZD37); Shanghai Science and Technology Innovation Action Plan(20JC1416900); Shanghai Science and Technology Innovation Action Plan(21N41900500)

α-Chiral azides are widely used in the fields of synthetic chemistry, medicinal chemistry and life science. Owing to α-chiral azides can be used for the diverse synthesis of α-chiral amine derivatives and nitrogen-containing heterocycles, and its azido group is also a pharmacophore, the efficient synthesis of α-chiral azides is highly important for drug discovery and development. Along with the incorporation of chiral quaternary carbon that can increase the three-dimensional stereospecificity of molecules has become an effective strategy to improve the bioactivity and druggability in drug design and development, the development of catalytic asymmetric synthetic methods toward α-chiral tertiary azides featuring aza-quaternary carbon center is highly desirable to facilitate drug research. However, due to the adverse steric effects caused by the structure of azido group that is close to a straight line, and the challenge of distinguishing the substituents with less difference to construct the aza-quaternary carbon stereocenter, the catalytic asymmetric protocols with high enantioselectivity are relatively scarce. This review aims to summarize the advances of the past five years according to the following two strategies: asymmetric functionalizations of C—N₃ bond containing compounds and asymmetric azidations involving C—N₃ bond forming, as well as discusses the possible reaction mechanism, the advantages and disadvantages of different reactions, which would provide some references and inspiration for researchers engaged in organic synthesis and medicinal chemistry.

Key words: α-chiral tertiary azide, catalytic asymmetric synthesis, sodium azide, trimethylsilyl azide, electrophilic azidation, nucleophilic addition

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Yang Gao, Xuexin Zhang, Jinsheng Yu, Jian Zhou. Recent Advances in Catalytic Enantioselective Synthesis of α-Chiral Tertiary Azides^★[J]. Acta Chimica Sinica, 2023, 81(11): 1590-1608.

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Fig. & Tab. 24

Figure 1. The typical applications of α-chiral azides

Figure 2. Catalytic asymmetric strategies toward α-chiral tertiary azides

Figure 3. Asymmetric Diels-Alder reactions of vinyl azides with β,γ-unsaturated-α-ketoesters

Figure 4. Asymmetric [4+2] cycloaddition and the related tandem reactions between vinyl azides and aldimines

Figure 5. Asymmetric Mannich reaction of α-azido cyclic ketones with aldimines

Figure 6. Asymmetric Mannich reaction of α-azido cyclic ketones with isatin ketimines

Figure 7. Michael addition of α-azido indanones to nitroolefins

Figure 8. Asymmetric Michael addition of α-azido indanones to β,γ-unsaturated-α-ketoesters

Figure 9. Sulfonyl-PyBox enable kinetic resolution of α-tertiary azides

Figure 10. Diverse elaborations of chiral α-tertiary azidoketones and 3-azidooxindoles

Figure 11. Chiral Cu-catalyzed asymmetric dearomative electrophilic α-azidation of β-naphthols

Figure 12. Copper-catalyzed asymmetric dearomative azidation

Figure 13. Copper-catalyzed asymmetric electrophilic α-azidation of 3-trifluoromethylated oxindoles

Figure 14. Zn-catalyzed asymmetric electrophilic α-azidation of β-ketoester/amides

Figure 15. Asymmetric α-azidation of β-ketoesters catalyzed by cinchonidine

Figure 16. Asymmetric azidation of α-bromo cyclic ketoximes with NaN3

Figure 17. Asymmetric SN2X of α-bromo-α-cyanoesters with NaN3

Figure 18. Asymmetric kinetic resolution of α-bromo-α-cyanoesters with NaN3

Figure 19. Asymmetric oxidative azidation of ketoesters

Figure 20. Enantioselective Mn-catalyzed C—H azidation of indolines

Figure 21. Enzyme-catalyzed asymmetric hydroxyazidation of α-methyl styrene

Figure 22. Asymmetric haloazidation of allylic alcohols with TMSN3

Figure 23. Anionic CN-box/Cu catalyzed asymmetric radical azidation of acrylamides

Figure 24. Fe-catalyzed asymmetric radical carboazidation of α-aryl enones

References 48

[1]	(a) Grieß P. Justus Liebigs Ann. Chem. 1865, 135, 131.
	(b) Grieß P. Philos. Trans. R. Soc. London, 1864, 13, 377.
[2]	(a) Boyer J. H.; Canter F. C. Chem. Rev. 1954, 54, 1. doi: 10.1021/cr60167a001 pmid: 16444296
	(b) L’abbé. G. Chem. Rev. 1969, 69, 345. doi: 10.1021/cr60259a004 pmid: 16444296
	(c) Scriven E. F. V.; Turnbull K. Chem. Rev. 1988, 88, 297. doi: 10.1021/cr00084a001 pmid: 16444296
	(d) Bräse S.; Gil C.; Knepper K.; Zimmermann V. Angew. Chem., Int. Ed. 2005, 44, 5188. doi: 10.1002/anie.v44:33 pmid: 16444296
	(e) Lang S.; Murphy J. A. Chem. Soc. Rev. 2006, 35, 146. pmid: 16444296
	(f) Fu J.; Zanoni G.; Anderson E. A.; Bi X. Chem. Soc. Rev. 2017, 46, 7208. doi: 10.1039/C7CS00017K pmid: 16444296
	(g) Sivaguru P.; Ning Y.; Bi X. Chem. Rev. 2021, 121, 4253. doi: 10.1021/acs.chemrev.0c01124 pmid: 16444296
	(h) Bräse S.; Banert K. Organic Azides: Syntheses and Applications, Wiley, 2009. pmid: 16444296
[3]	(a) Meldal M.; Tornøe C. W. Chem. Rev. 2008, 108, 2952. doi: 10.1021/cr0783479 pmid: 27115045
	(b) Mamidyala S. K.; Finn M. G. Chem. Soc. Rev. 2010, 39, 1252. doi: 10.1039/b901969n pmid: 27115045
	(c) Golas P. L.; Matyjaszewski K. Chem. Soc. Rev. 2010, 39, 1338. doi: 10.1039/B901978M pmid: 27115045
	(d) Tiwari V. K.; Mishra B. B.; Mishra K. B.; Mishra N.; Singh A. S.; Chen X. Chem. Rev. 2016, 116, 3086. doi: 10.1021/acs.chemrev.5b00408 pmid: 27115045
	(e) Kacprzak K.; Skiera I.; Piasecka M.; Paryzek Z. Chem. Rev. 2016, 116, 5689. doi: 10.1021/acs.chemrev.5b00302 pmid: 27115045
[4]	Beenhouwer D. O.; Rankin J. A.; Mellors J. W. Antiviral Res. 1992, 19, 43. doi: 10.1016/0166-3542(92)90055-A
[5]	Klumpp K.; Lévêque V.; Pogam S. L.; Ma H.; Jiang W.-R.; Kang H.; Granycome C.; Singer M.; Laxton C.; Hang J. Q.; Sarma K.; Smith D. B.; Heindl D.; Hobbs J. C.; Merrett J. H.; Symons J.; Cammack N.; Martin J. A.; Devos R.; Nájera I. J. Biol. Chem. 2006, 281, 3793. doi: 10.1074/jbc.M510195200 pmid: 16316989
[6]	Sun L.; Peng Y.; Yu W.; Zhang Y.; Liang L.; Song C.; Hou J.; Qiao Y.; Wang Q.; Chen J.; Wu M.; Zhang D.; Li E.; Han Z.; Zhao Q.; Jin X.; Zhang B.; Huang Z.; Chai J.; Wang J.-H.; Chang J. J. Med. Chem. 2020, 63, 8554. doi: 10.1021/acs.jmedchem.0c00940 pmid: 32678592
[7]	(a) Lao Z.; Toy P. H. Beilstein J. Org. Chem. 2016, 12, 2577. doi: 10.3762/bjoc.12.253
	(b) Palacios F.; Alonso C.; Aparicio D.; Rubiales G.; Santos J. M. Tetrahedron 2007, 63, 523. doi: 10.1016/j.tet.2006.09.048
	(c) Haldón E.; Nicasio M. C.; Pérez P. J. Org. Biomol. Chem. 2015, 13, 9528. doi: 10.1039/C5OB01457C
	(d) Uchida T.; Katsuki T. Chem. Rec. 2014, 14, 117. doi: 10.1002/tcr.v14.1
	(e) Frost J. R.; Pearson C. M.; Snaddon T. N.; Booth R. A.; Turner R. M.; Gold J.; Shaw D. M.; Gaunt M. J.; Ley S. V. Chem. Eur. J. 2015, 21, 13261. doi: 10.1002/chem.v21.38
[8]	(a) Shibatomi K.; Soga Y.; Narayama A.; Fujisawa I.; Iwasa S. J. Am. Chem. Soc. 2012, 134, 9836. doi: 10.1021/ja304806j pmid: 29160074
	(b) Bosmani A.; Pujari S. A.; Besnard C.; Guénée L.; Poblador-Bahamonde A. I.; Lacour J. Chem. Eur. J. 2017, 23, 8678. doi: 10.1002/chem.v23.36 pmid: 29160074
	(c) Fernández-Valparis J.; Romea P.; Urpí F.; Font-Bardia M. Org. Lett. 2017, 19, 6400. doi: 10.1021/acs.orglett.7b03255 pmid: 29160074
[9]	(a) Ding P.-G.; Hu X.-S.; Zhou F.; Zhou J. Org. Chem. Front. 2018, 5, 1542. doi: 10.1039/C8QO00138C
	(b) Ge L.; Chiou M.-F.; Li Y.; Bao H. Green Synth. Catal. 2020, 1, 86.
	(c) Wei F.; Yu X.; Xiao Q. Chin. J. Org. Chem. 2023, 43, 1365. (in Chinese) doi: 10.6023/cjoc202209022
	( 魏芳, 余鑫, 肖强, 有机化学, 2023, 43, 1365.) doi: 10.6023/cjoc202209022
[10]	Liu Z.; Liao P.; Bi X. Org. Lett. 2014, 16, 3668. doi: 10.1021/ol501661k
[11]	(a) Wang Y.-F.; Toh K. K.; Ng E. P. J.; Chiba S. J. Am. Chem. Soc. 2011, 133, 6411. doi: 10.1021/ja200879w
	(b) Wang Y.-F.; Toh K. K.; Lee J.-Y.; Chiba S. Angew. Chem., Int. Ed. 2011, 50, 5927. doi: 10.1002/anie.v50.26
	(c) Jung N.; Bräse S. Angew. Chem., Int. Ed. 2012, 51, 12169. doi: 10.1002/anie.v51.49
	(d) Xuan J.; Xia X.-D.; Zeng T.-T.; Feng Z.-J.; Chen J.-R.; Lu L.-Q.; Xiao W.-J. Angew. Chem., Int. Ed. 2014, 53, 5653. doi: 10.1002/anie.v53.22
	(e) Farney E. P.; Yoon T. P. Angew. Chem., Int. Ed. 2014, 53, 793. doi: 10.1002/anie.v53.3
	(f) Hu B.; DiMagno S. G. Org. Biomol. Chem. 2015, 13, 3844. doi: 10.1039/C5OB00099H
	(g) Hayashi H.; Kaga A.; Chiba S. J. Org. Chem. 2017, 82, 11981. doi: 10.1021/acs.joc.7b02455
	(h) Ning Y.; Ji Q.; Liao P.; Anderson E. A.; Bi X. Angew. Chem., Int. Ed. 2017, 56, 13805. doi: 10.1002/anie.v56.44
	(i) Ning Y.; Zhao X.-F.; Wu Y.-B.; Bi X. Org. Lett. 2017, 19, 6240. doi: 10.1021/acs.orglett.7b03204
	(j) Kanchupalli V.; Katukojvala S.; Angew. Chem., Int. Ed. 2018, 57, 5433. doi: 10.1002/anie.v57.19
	(k) Zhong Z.; Xiao Z.; Liu X.; Cao W.; Feng X. Chem. Sci. 2020, 11, 11492. Also see ref. 2f. doi: 10.1039/D0SC03776A
[12]	(a) Gu P.; Su Y.; Wu X. P.; Sun J.; Liu W.; Xue P.; Li R. Org. Lett. 2012, 14, 2246. doi: 10.1021/ol3006437
	(b) López E.; López L. A. Angew. Chem., Int. Ed. 2017, 56, 5121. doi: 10.1002/anie.v56.18
[13]	Thirupathi N.; Wei F.; Tung C.-H.; Xu Z. Nat. Commun. 2019, 10, 3158. doi: 10.1038/s41467-019-11134-8 pmid: 31320649
[14]	Nakanishi T.; Kikuchi J.; Kaga A.; Chiba S.; Terada M. Chem. Eur. J. 2020, 26, 8230. doi: 10.1002/chem.v26.37
[15]	Chowdari N. S.; Ahmad M.; Albertshofer K.; Tanaka F.; Barbas C. F. Org. Lett. 2006, 8, 2839. pmid: 16774270
[16]	Martínez-Castañeda Á.; Kędziora K.; Lavandera I.; Rodríguez- Solla H.; Concellón C.; Amo V. Chem. Commun. 2014, 50, 2598. doi: 10.1039/c3cc49371g
[17]	McNulty J.; Zepeda-Velázquez C. Angew. Chem., Int. Ed. 2014, 53, 8450. doi: 10.1002/anie.v53.32
[18]	(a) Weidner K.; Sun Z.; Kumagai N.; Shibasaki M. Angew. Chem., Int. Ed. 2015, 54, 6236. doi: 10.1002/anie.v54.21
	(b) Sun Z.; Weidner K.; Kumagai N.; Shibasaki M. Chem. Eur. J. 2015, 21, 17574. doi: 10.1002/chem.v21.49
	(c) Noda H.; Amemiya F.; Weidner K.; Kumagai N.; Shibasaki M. Chem. Sci. 2017, 8, 3260. doi: 10.1039/C7SC00330G
[19]	Okumuş S.; Tanyeli C.; Demir A. S. Tetrahedron Lett. 2014, 55, 4302. doi: 10.1016/j.tetlet.2014.06.018
[20]	Ye X.; Pan Y.; Yang X. Chem. Commun. 2020, 56, 98. doi: 10.1039/C9CC08000G
[21]	Karahan S.; Tanyeli C. Org. Biomol. Chem. 2020, 18, 479. doi: 10.1039/c9ob02208b pmid: 31845945
[22]	Ding P.-G.; Zhou F.; Wang X.; Zhao Q.-H.; Yu J.-S.; Zhou J. Chem. Sci. 2020, 11, 3852. doi: 10.1039/D0SC00475H
[23]	Ding P.-G.; Hu X.-S.; Yu J.-S.; Zhou J. Org. Lett. 2020, 22, 8578. doi: 10.1021/acs.orglett.0c03178
[24]	For a review: (a) Wang C.; Zhou F.; Zhou J. Chin. J. Org. Chem. 2020, 40, 3065. (in Chinese) doi: 10.6023/cjoc202005020 pmid: 31117717
	王才, 周锋, 周剑, 有机化学, 2020, 40, 3065.) pmid: 31117717
	For selected examples: (b) Meng J.; Fokin V. V.; Finn M. G. Tetrahedron Lett. 2005, 46, 4543. doi: 10.1016/j.tetlet.2005.05.019 pmid: 31117717
	(c) Alexander J. R.; Ott A. A.; Liu E.-C.; Topczewski J. J. Org. Lett. 2019, 21, 4355. doi: 10.1021/acs.orglett.9b01556 pmid: 31117717
	(d) Liu E.-C.; Topczewski J. J. J. Am. Chem. Soc. 2019, 141, 5135. doi: 10.1021/jacs.9b01091 pmid: 31117717
[25]	Yang X.; Birman V. B. Chem. Eur. J. 2011, 17, 11296. doi: 10.1002/chem.v17.40
[26]	Ott A. A.; Goshey C. S.; Topczewski J. J. J. Am. Chem. Soc. 2017, 139, 7737. doi: 10.1021/jacs.7b04203
[27]	Ye P.; Feng A.; Wang L.; Cao M.; Zhu R.; Liu L. Nat. Commun. 2022, 13, 1621. doi: 10.1038/s41467-022-29319-z
[28]	Gong Y.; Wang C.; Zhou F.; Liao K.; Wang X.-Y.; Sun Y.; Zhang Y.-X.; Tu Z.; Wang X.; Zhou J. Angew. Chem., Int. Ed. 2023, 62, e202301470. doi: 10.1002/anie.v62.18
[29]	(a) Zhu R.-Y.; Chen L.; Hu X.-S.; Zhou F.; Zhou J. Chem. Sci. 2020, 11, 97. doi: 10.1039/C9SC04938J
	(b) Liao K.; Gong Y.; Zhu R.-Y.; Wang C.; Zhou F.; Zhou J. Angew. Chem., Int. Ed. 2021, 60, 8488. doi: 10.1002/anie.v60.15
[30]	(a) Zhdankin V. V. Hypervalent Iodine Chemistry: Preparation, Structure and Synthetic Application of Polyvalent Iodine Compounds, John Wiley & Sons Ltd., New York, 2014. pmid: 26861673
	(b) Yoshimura A.; Zhdankin V. V. Chem. Rev. 2016, 116, 3328. doi: 10.1021/acs.chemrev.5b00547 pmid: 26861673
[31]	(a) Simonet-Davin R.; Waser J. Synthesis 2023, 55, 1652. doi: 10.1055/a-1966-4974
	(b) Mironova I. A.; Kirsch S. F.; Zhdankin V. V.; Yoshimura A.; Yusubov M. S. Eur. J. Org. Chem. 2022, 2022, e202200754. doi: 10.1002/ejoc.v2022.34
[32]	Deng Q.-H.; Bleith T.; Wadepohl H.; Gade L. H. J. Am. Chem. Soc. 2013, 135, 5356. doi: 10.1021/ja402082p
[33]	Wang C.-J.; Sun J.; Zhou W.; Xue J.; Ren B.-T.; Zhang G.-Y.; Mei Y.-L.; Deng Q.-H. Org. Lett. 2019, 21, 7315. doi: 10.1021/acs.orglett.9b02604
[34]	Lin C.-Z.; Jiang L.-F.; Zhang G.-Y.; Zhou F.-S.; Wu S.-H.; Jing C.; Deng Q.-H. Chem. Commun. 2023, 59, 7831. doi: 10.1039/D3CC01438J
[35]	Chen Y.-X.; Huo T.; Yin Q.; Jiang L.-F.; Cheng X.; Ma H.-X.; Jiang Y.-X.; Sun M.-Z.; Deng Q.-H. Org. Lett. 2023, 25, 2739. doi: 10.1021/acs.orglett.3c01005
[36]	He C.; Wu Z.; Zhou Y.; Cao W.; Feng X. Org. Chem. Front. 2022, 9, 703. doi: 10.1039/D1QO01634B
[37]	Tiffner M.; Stockhammer L.; Schörgenhumer J.; Röser K.; Waser M. Molecules 2018, 23, 1142. doi: 10.3390/molecules23051142
[38]	Examples for constructing of α-chiral secondary azides using NaN₃: (a) Taylor M. S.; Zalatan D. N.; Lerchner A. M.; Jacobsen E. N. J. Am. Chem. Soc. 2005, 127, 1313. doi: 10.1021/ja044999s pmid: 15669872
	(b) Huang X.; Bergsten T. M.; Groves J. T. J. Am. Chem. Soc. 2015, 137, 5300. doi: 10.1021/jacs.5b01983 pmid: 15669872
[39]	Gomes R. S.; Corey E. J. J. Am. Chem. Soc. 2019, 141, 20058. doi: 10.1021/jacs.9b12315
[40]	Zhang X.; Ren J.; Tan S. M.; Tan D.; Lee R.; Tan C.-H. Science 2019, 363, 400. doi: 10.1126/science.aau7797 pmid: 30679372
[41]	Ren J.; Ban X.; Zhang X.; Tan S. M.; Lee R.; Tan C.-H. Angew. Chem., Int. Ed. 2020, 59, 9055. doi: 10.1002/anie.v59.23
[42]	Uyanik M.; Sahara N.; Tsukahara M.; Hattori Y.; Ishihara K. Angew. Chem., Int. Ed. 2020, 59, 17110. doi: 10.1002/anie.v59.39
[43]	Cao M.; Wang H.; Ma Y.; Tung C.-H.; Liu L. J. Am. Chem. Soc. 2022, 144, 15383. doi: 10.1021/jacs.2c07089
[44]	Wu J.-F.; Wan N.-W.; Li Y.-N.; Wang Q.-P.; Cui B.-D.; Han W.-Y.; Chen Y.-Z. iScience 2021, 24, 102883. doi: 10.1016/j.isci.2021.102883
[45]	Zhou P.; Lin L.; Chen L.; Zhong X.; Liu X.; Feng X. J. Am. Chem. Soc. 2017, 139, 13414. doi: 10.1021/jacs.7b06029
[46]	Seidl F. J.; Min C.; Lopez J. A.; Burns N. Z. J. Am. Chem. Soc. 2018, 140, 15646. doi: 10.1021/jacs.8b10799
[47]	Wu L.; Zhang Z.; Wu D.; Wang F.; Chen P.; Lin Z.; Liu G. Angew. Chem., Int. Ed. 2021, 60, 6997. doi: 10.1002/anie.v60.13
[48]	Liu W.; Pu M.; He J.; Zhang T.; Dong S.; Liu X.; Wu Y.-D.; Feng X. J. Am. Chem. Soc. 2021, 143, 11856. doi: 10.1021/jacs.1c05881

α-手性三级叠氮化合物的不对称催化合成新进展^★

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[5]	CAO Zhi-Juan, LIU Cai-Yun, LU Jian-Zhong. Study of New Chemiluminescence Technique--Recognition of Sodium Azide by External Reference Method [J]. Acta Chimica Sinica, 2004, 62(8): 794-798.

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Recent Advances in Catalytic Enantioselective Synthesis of α-Chiral Tertiary Azides★

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α-手性三级叠氮化合物的不对称催化合成新进展^★

Recent Advances in Catalytic Enantioselective Synthesis of α-Chiral Tertiary Azides^★