SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 10: 3367 - 3387

DOI: https://doi.org/10.6023/cjoc202304030

Catalytic Enantioselective Preparation of Chiral Allylsilanes

  • Xin Kuang ,
  • Changhua Ding ,
  • Yichen Wu ,
  • Peng Wang
Expand
  • a College of Science, Shanghai University, Shanghai 201900
    b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
    c CAS Key Laboratory of Energy Regulation Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
    d School of Chemistry and Material Sciences, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024
*E-mail: ;

Received date: 2023-04-21

  Revised date: 2023-05-11

  Online published: 2023-05-25

Supported by

National Key R&D Program of China(2021YFA1500200); National Natural Science Foundation of China(22101291); National Natural Science Foundation of China(22171277); National Natural Science Foundation of China(21821002); Shanghai Rising-Star Program(20QA1411400)

Fold

Abstract

Chiral allylsilanes, a versatile linchpin, are widely used in the area of asymmetric synthesis. Therefore, the development of efficient methodologies for the preparation of the enantioenriched allylsilanes has attracted great attention. Significant advances have been made in the catalytic enantioselective preparation of chiral allylsilanes by virtue of the rapid developments in asymmetric catalysis. The advances in the construction of chiral allylsilanes and their synthetic applications are summarized.

Key words： chiral allylsilanes; asymmetric catalysis; catalytic synthesis

Cite this article

Xin Kuang , Changhua Ding , Yichen Wu , Peng Wang . Catalytic Enantioselective Preparation of Chiral Allylsilanes[J]. Chinese Journal of Organic Chemistry, 2023 , 43(10) : 3367 -3387 . DOI: 10.6023/cjoc202304030

References

[1]
(a) Langkopf E.; Schinzer D. Chem. Rev. 1995, 95, 1375.
[1]
(b) Yamamoto Y.; Asao N. Chem. Rev. 1993, 93, 2207.
[1]
(c) Chabaud L.; James P.; Landais Y. Eur. J. Org. Chem. 2004, 2004, 3173.
[2]
Auner N.; Weis J. Organosilicon Chemistry V: From Molecules to Materials, Wiley-VCH, Weinheim, Germany, 2004.
[3]
(a) Showell G. A.; Mills J. S. Drug Discovery Today 2003, 8, 551.
[3]
(b) Min G. K.; Hernández D.; Skrydstrup T. Acc. Chem. Res. 2013, 46, 457.
[3]
(c) Franz A. K.; Wilson S. O. J. Med. Chem. 2013, 56, 388.
[4]
(a) Chan T. H.; Wang D. Chem. Rev. 1992, 92, 995.
[4]
(b) Fleming I.; Barbero A.; Walter D. Chem. Rev. 1997, 97, 2063.
[4]
(c) Masse C. E.; Panek J. S. Chem. Rev. 1995, 95, 1293.
[5]
(a) Kira M.; Kobayashi M.; Sakurai H. Tetrahedron Lett. 1987, 28, 4081.
[5]
(b) Kira M.; Sato K.; Sakurai H. J. Am. Chem. Soc. 1990, 112, 257.
[5]
(c) Hosomi A.; Endo M.; Sakurai H. Chem. Lett. 1976, 5, 941.
[6]
Chan T. H.; Fleming I. Synthesis 1979, 761.
[7]
(a) Sarkar T. K. Synthesis 1990, 969.
[7]
(b) Sarkar T. K. Synthesis 1990, 1101.
[8]
Bhushan V.; Lohray B. B.; Enders D. Tetrahedron Lett. 1993, 34, 5067.
[9]
(a) Fleming I.; Thomas A. P. J. Chem. Soc., Chem. Commun. 1986, 1456.
[9]
(b) Buckle M. J. C.; Fleming I. Tetrahedron Lett. 1993, 34, 2383.
[10]
(a) Mikami K.; Maeda T.; Kishi N.; Nakai T. Tetrahedron Lett. 1984, 25, 5151.
[10]
(b) Sparks M. A.; Panek J. S. J. Org. Chem. 1991, 56, 3431.
[11]
(a) Landais Y.; Planchenault D.; Weber V. Tetrahedron Lett. 1994, 35, 9549.
[11]
(b) Bulugahapitiya P.; Landais Y.; Parra-Rapado L.; Planchenault D.; Weber V. J. Org. Chem. 1997, 62, 1630.
[12]
(a) Bourque L. E.; Cleary P. A.; Woerpel K. A. J. Am. Chem. Soc. 2007, 129, 12602.
[12]
(b) Hayashi S.; Hirano K.; Yorimitsu H.; Oshima K. J. Am. Chem. Soc. 2007, 129, 12650.
[12]
(c) Li D.; Tanaka T.; Ohmiya H.; Sawamura M. Org. Lett. 2010, 12, 3344.
[12]
(d) Nagao K.; Yokobori U.; Makida Y.; Ohmiya H.; Sawamura M. J. Am. Chem. Soc. 2012, 134, 8982.
[12]
(e) Yasuda Y.; Nagao K.; Shido Y.; Mori S.; Ohmiya H.; Sawamura M. Chem.-Eur. J. 2015, 21, 9666.
[13]
(a) Suginome M.; Ohmura T.; Miyake Y.; Mitani S.; Ito Y.; Murakami M. J. Am. Chem. Soc. 2003, 125, 11174.
[13]
(b) Ohmura T.; Suginome M. Org. Lett. 2006, 8, 2503.
[14]
Hayashi T.; Konishi M.; Ito H.; Kumada M. J. Am. Chem. Soc. 1982, 104, 4962.
[15]
(a) Hayashi T. Acc. Chem. Res. 2000, 33, 354.
[15]
(b) Gibson S. E.; Rudd M. Adv. Synth. Catal. 2007, 349, 781.
[15]
(c) Han J. W.; Hayashi T. Tetrahedron: Asymmetry 2010, 21, 2193.
[15]
(d) Wilkinson J. R.; Nuyen C. E.; Carpenter T. S.; Harruff S. R.; Van Hoveln R. ACS Catal. 2019, 9, 8961.
[16]
Hayashi T.; Kabeta K.; Yamamoto T.; Tamao K.; Kumada M. Tetrahedron Lett. 1983, 24, 5661.
[17]
Hayashi T.; Matsumoto Y.; Morikawa I.; Ito Y. Tetrahedron: Asymmetry 1990, 1, 151.
[18]
Ohmura H.; Matsuhashi H.; Tanaka M.; Kuroboshi M.; Hiyama T.; Hatanaka Y.; Goda K. J. Organomet. Chem. 1995, 499, 167.
[19]
(a) Okada T.; Morimoto T.; Achiwa K. Chem. Lett. 1990, 19, 999.
[19]
(b) Sakuraba S.; Okada T.; Morimoto T.; Achiwa K. Chem. Pharm. Bull. 1995, 43, 927.
[20]
Marinetti A. Tetrahedron Lett. 1994, 35, 5861.
[21]
Hayashi T.; Han Jin, W.; Takeda A.; Tang T.; Nohmi K.; Mukaide K.; Tsuji H.; Uozumi Y. Adv. Synth. Catal. 2001, 343, 279.
[22]
Han J. W.; Hayashi T. Tetrahedron: Asymmetry 2002, 13, 325.
[23]
Park H. S.; Han J. W.; Shintani R.; Hayashi T. Tetrahedron: Asymmetry 2013, 24, 418.
[24]
Hayashi T.; Kabeta K. Tetrahedron Lett. 1985, 26, 3023.
[25]
Han J. W.; Tokunaga N.; Hayashi T. Helv. Chim. Acta 2002, 85, 3848.
[26]
Hatanaka Y.; Goda K.; Yamashita F.; Hiyama T. Tetrahedron Lett. 1994, 35, 7981.
[27]
Sang H.-L.; Yu S.; Ge S. Chem. Sci. 2018, 9, 973.
[28]
Wen H.; Wang K.; Zhang Y.; Liu G.; Huang Z. ACS Catal. 2019, 9, 1612.
[29]
Huang Y.-H.; Wu Y.; Zhu Z.; Zheng S.; Ye Z.; Peng Q.; Wang P. Angew. Chem., Int. Ed. 2022, 61, e202113052.
[30]
Wang L.; Lu W.; Zhang J.; Chong Q.; Meng F. Angew. Chem., Int. Ed. 2022, 61, e202205624.
[31]
Li K.; Nie M.; Tang W. Green Synth. Catal. 2020, 1, 171.
[32]
Xu J.-L.; Xu Z.-Y.; Wang Z.-L.; Ma W.-W.; Sun X.-Y.; Fu Y.; Xu Y.-H. J. Am. Chem. Soc. 2022, 144, 5535.
[33]
Li S.; Xu J.-L.; Xu Y.-H. Org. Lett. 2022, 24, 6054.
[34]
Liu T.; Mao X.-R.; Song S.; Chen Z.-Y.; Wu Y.; Xu L.-P.; Wang P. Angew. Chem., Int. Ed. 2023, 62, e202216878.
[35]
Chang X.; Ma P.-L.; Chen H.-C.; Li C.-Y.; Wang P. Angew. Chem., Int. Ed. 2020, 59, 8937.
[36]
Matsumoto Y.; Ohno A.; Hayashi T. Organometallics 1993, 12, 4051.
[37]
Hayashi T.; Ohno A.; Lu S.; Matsumoto Y.; Fukuyo E.; Yanagi K. J. Am. Chem. Soc. 1994, 116, 4221.
[38]
Delvos L. B.; Vyas D. J.; Oestreich M. Angew. Chem., Int. Ed. 2013, 52, 4650.
[39]
McQuade D.; Park J. Synthesis 2012, 44, 1485.
[40]
Oestreich M.; Delvos L.; Hensel A. Synthesis 2014, 46, 2957.
[41]
Oestreich M.; Delvos L. Synthesis 2015, 47, 924.
[42]
Takeda M.; Shintani R.; Hayashi T. J. Org. Chem. 2013, 78, 5007.
[43]
Hensel A.; Oestreich M. Chem.-Eur. J. 2015, 21, 9062.
[44]
(a) Morizawa Y.; Oda H.; Oshima K.; Nozaki H. Tetrahedron Lett. 1984, 25, 1163.
[44]
(b) Weickgenannt A.; Oestreich M. Chem.-Eur. J. 2010, 16, 402.
[45]
(a) Bobek M.; Kavai I.; De Clercq E. J. Med. Chem. 1987, 30, 1494.
[45]
(b) Leriche C.; He X.; Chang C.-W. T.; Liu H.-W. J. Am. Chem. Soc. 2003, 125, 6348.
[45]
(c) Lamy C.; Hofmann J.; Parrot-Lopez H.; Goekjian P. Tetrahedron Lett. 2007, 48, 6177.
[45]
(d) Juncosa J. I.; Takaya K.; Le H. V.; Moschitto M. J.; Weerawarna P. M.; Mascarenhas R.; Liu D.; Dewey S. L.; Silverman R. B. J. Am. Chem. Soc. 2018, 140, 2151.
[46]
Paioti P. H. S.; Del Pozo J.; Mikus M. S.; Lee J.; Koh M. J.; Romiti F.; Torker S.; Hoveyda A. H. J. Am. Chem. Soc. 2019, 141, 19917.
[47]
Gao P.; Gao L.; Xi L.; Zhang Z.; Li S.; Shi Z. Org. Chem. Front. 2020, 7, 2618.
[48]
Hayashi T.; Iwamura H.; Uozumi Y. Tetrahedron Lett. 1994, 35, 4813.
[49]
Kacprzynski M. A.; May T. L.; Kazane S. A.; Hoveyda A. H. Angew. Chem., Int. Ed. 2007, 46, 4554.
[50]
Shintani R.; Takatsu K.; Takeda M.; Hayashi T. Angew. Chem., Int. Ed. 2011, 50, 8656.
[51]
Jung B.; Hoveyda A. H. J. Am. Chem. Soc. 2012, 134, 1490.
[52]
Shido Y.; Yoshida M.; Tanabe M.; Ohmiya H.; Sawamura M. J. Am. Chem. Soc. 2012, 134, 18573.
[53]
Hayashi T.; Konishi M.; Okamoto Y.; Kabeta K.; Kumada M. J. Org. Chem. 1986, 51, 3772.
[54]
(a) Gu J.; Wang X.; Xue W.; Gong H. Org. Chem. Front. 2015, 2, 1411.
[54]
(b) Wang X.; Dai Y.; Gong H. Top. Curr. Chem. 2016, 374, No. 43.
[54]
(c) Pang X.; Shu X.-Z. Chem.-Eur. J. 2023, 29, e202203362.
[55]
Hofstra J. L.; Cherney A. H.; Ordner C. M.; Reisman S. E. J. Am. Chem. Soc. 2018, 140, 139.
[56]
Levi Knippel J.; Ni A. Z.; Schuppe A. W.; Buchwald S. L. Angew. Chem., Int. Ed. 2022, 61, e202212630.
[57]
Bagheri V.; Doyle M. P.; Taunton J.; Claxton E. E. J. Org. Chem. 1988, 53, 6158.
[58]
Davies H. M. L.; Hansen T.; Rutberg J.; Bruzinski P. R. Tetrahedron Lett. 1997, 38, 1741.
[59]
Sambasivan R.; Ball Z. T. J. Am. Chem. Soc. 2010, 132, 9289.
[60]
Chen D.; Zhang X.; Qi W.-Y.; Xu B.; Xu M.-H. J. Am. Chem. Soc. 2015, 137, 5268.
[61]
Chen D.; Zhu D.-X.; Xu M.-H. J. Am. Chem. Soc. 2016, 138, 1498.
[62]
Wu J.; Chen Y.; Panek J. S. Org. Lett. 2010, 12, 2112.
[63]
Wu J.; Panek J. S. J. Org. Chem. 2011, 76, 9900.
[64]
Lee K.; Hoveyda A. H. J. Am. Chem. Soc. 2010, 132, 2898.
[65]
Lee K.; Wu H.; Haeffner F.; Hoveyda A. H. Organometallics 2012, 31, 7823.
[66]
Mita T.; Sugawara M.; Saito K.; Sato Y. Org. Lett. 2014, 16, 3028.
[67]
Da B.-C.; Liang Q.-J.; Luo Y.-C.; Ahmad T.; Xu Y.-H.; Loh T.-P. ACS Catal. 2018, 8, 6239.
[68]
Meng F.-F.; Xie J.-H.; Xu Y.-H.; Loh T.-P. ACS Catal. 2018, 8, 5306.
[69]
Wang X.-L.; Yin X.-H.; Xiao J.-Z.; Jia X.-S.; Yin L. Chin. J. Chem. 2021, 39, 1916.
[70]
Gerdin M.; Moberg C. Adv. Synth. Catal. 2005, 347, 749.
[71]
Ohmura T.; Taniguchi H.; Suginome M. J. Am. Chem. Soc. 2006, 128, 13682.
[72]
Saito N.; Kobayashi A.; Sato Y. Angew. Chem., Int. Ed. 2012, 51, 1228.
[73]
Ogoshi S.; Tonomori K.; Oka M.; Kurosawa H. J. Am. Chem. Soc. 2006, 128, 7077.
[74]
Han S. B.; Gao X.; Krische M. J. J. Am. Chem. Soc. 2010, 132, 9153.
[75]
Zhang Y.; Huang J.; Guo Y.; Li L.; Fu Z.; Huang W. Angew. Chem., Int. Ed. 2018, 57, 4594.
[76]
(a) Nakao Y.; Imanaka H.; Sahoo A. K.; Yada A.; Hiyama T. J. Am. Chem. Soc. 2005, 127, 6952.
[76]
(b) Nakao Y.; Sahoo A.; Yada A.; Chen J.; Hiyama T. Sci. Technol. Adv. Mater. 2006, 7, 536.
[76]
(c) Nakao Y.; Imanaka H.; Chen J.; Yada A.; Hiyama T. J. Organomet. Chem. 2007, 692, 585.
[77]
Shintani R.; Ichikawa Y.; Hayashi T.; Chen J.; Nakao Y.; Hiyama T. Org. Lett. 2007, 9, 4643.
Options
Outlines

/

〈 〉