金属卡宾参与的对映选择性去对称化反应研究进展
收稿日期: 2022-06-21
修回日期: 2022-07-04
网络出版日期: 2022-07-14
基金资助
国家自然科学基金(92056104)
Research Progress on Enantioselective Desymmetrization Reactions Involving Metal Carbenes
Received date: 2022-06-21
Revised date: 2022-07-04
Online published: 2022-07-14
Supported by
National Natural Science Foundation of China(92056104)
滕明瑜 , 韩涛 , 黄恩和 , 叶龙武 . 金属卡宾参与的对映选择性去对称化反应研究进展[J]. 有机化学, 2022 , 42(10) : 3295 -3301 . DOI: 10.6023/cjoc202206041
Metal carbenes have been widely applied in organic synthesis, and they can undergo a variety of chemical transformations due to their versatile reactivities. In this review, the desymmetrization of C—H insertion reaction, Buchner reaction, Si—H insertion reaction and B—H insertion reaction involving metal carbenes is introduced according to the different reaction types of metal carbenes. Under the catalysis of chiral rhodium, ruthenium and copper catalysts, chiral carbocycles, heterocycles, organosilicons and organoborons can be obtained with high enantioselectivity, which greatly enriches the development of asymmetric synthetic chemistry.
Key words: diazo compounds; metal carbene; desymmetrization; aymmetric synthesis
| [1] | For selected reviews on metal carbenes from diazo compounds, see: (a) Dong S.; Liu X.; Feng, X. Acc. Chem. Res. 2022, 55, 415. |
| [1] | (b) Wang, F.; Zhang, Z.; Huang, F. Chin. J. Org. Chem. 2021, 41, 144. (in Chinese). |
| [1] | (王飞雨, 张志朋, 黄菲, 有机化学, 2021, 41, 144.) |
| [1] | (c) Zhu, D.; Chen, L.; Fan, H.; Yao, Q.; Zhu, S. Chem. Soc. Rev. 2020, 49, 908. |
| [1] | (d) Wei, F.; Song, C.; Ma, Y.; Zhou, L.; Tung, C.-H.; Xu, Z. Sci. Bull. 2015, 60, 1479. |
| [1] | (e) Ford, A.; Miel, H.; Ring, A.; Slattery, C. N.; Maguire, A. R.; McKervey, M. A. Chem. Rev. 2015, 115, 9981. |
| [1] | (f) Zhao, X.; Zhang, Y.; Wang, J. Chem. Commun. 2012, 48, 10162. |
| [1] | (g) Michael, P. D.; Richard, D.; Maxim, R.; Zhou, L. Chem. Rev. 2010, 110, 704. |
| [1] | (h) Zhang, Z.; Wang, J. Tetrahedron 2008, 64, 6577. |
| [1] | (i) Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861. |
| [1] | (j) Michael, P. D.; David, C. F. Chem. Rev. 1998, 98, 911. |
| [1] | (k) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091. |
| [2] | For selected reviews on metal carbenes from alkynes, see: (a) Hong, F.-L.; Ye, L.-W. Acc. Chem. Res. 2020, 53, 2003. |
| [2] | (b) Ye, L.-W.; Zhu, X.-Q.; Sahani, R. L.; Xu, Y.; Qian, P.-C.; Liu, R.-S. Chem. Rev. 2021, 121, 9039. |
| [2] | (c) Sahani, R. L.; Ye, L.-W.; Liu, R.-S. Adv. Organomet. Chem. 2020, 73, 195. |
| [2] | (d) Chen, L.; Chen, K; Zhu, S. Chem 2018, 4, 1208. |
| [2] | (e) Liao, Y.; Zhu, L.; Yu, Y.; Chen, G.; Huang, X. Chin. J. Org. Chem. 2017, 37, 2785. (in Chinese). |
| [2] | (廖云, 朱磊, 俞颖华, 陈贵, 黄学良, 有机化学, 2017, 37, 2785.) |
| [2] | (f) Zi, W.; Toste, F. D. Chem. Soc. Rev. 2016, 45, 4567. |
| [2] | (g) Harris, R. J.; Widenhoefer, R. A. Chem. Soc. Rev. 2016, 45, 4533. |
| [2] | (h) Zheng, Z.; Wang, Z.; Wang, Y.; Zhang, L. Chem. Soc. Rev. 2016, 45, 4448. |
| [2] | (i) Jia, M.; Ma, S. Angew. Chem., Int. Ed. 2016, 55, 9134. |
| [3] | Brooks, W. H.; Guida, W. C.; Daniel, K. G. Curr. Top. Med. Chem. 2011, 11, 760. |
| [4] | For selected reviews on desymmetrization reactions, see: (a) Xu, Y.; Zhai, T.-Y.; Xu, Z.; Ye, L.-W. Trends Chem. 2022, 4, 191. |
| [4] | (b) Marcos, E.; Daniel, G.; Javier, T.; Santiago, D.-O.; Carlos del, P. Eur. J. Org. Chem. 2021, 21, 2923. |
| [4] | (c) Liu, W.; Yang, X. Asian J. Org. Chem. 2021, 10, 692. |
| [4] | (d) Wang, C.; Zhou, F.; Zhou, J. Chin. J. Org. Chem. 2020, 40, 3065. (in Chinese). |
| [4] | (王才, 周锋, 周剑, 有机化学, 2020, 40, 3065.) |
| [4] | (e) Kimberly, S. P. Tetrahedron Lett. 2015, 56, 6523. |
| [5] | Kennedy, M.; McKervey, M. A.; Maguire, A. R.; Roos, G. H. P. J. Chem. Soc., Chem. Commun. 1990, 361. |
| [6] | For selected examples, see: (a) Shintani, R.; Sannohe Y.; Tsuji, T.; Hayashi, T. J. Am. Chem. Soc. 2006, 128, 16038. |
| [6] | (b) Doyle, M. P.; Wang, Y.; Ghorbani, P.; Bappert, E. Org. Lett. 2005, 7, 5035. |
| [6] | (c) Doyle, M. P.; Hu, W.; Wee, A. G. H.; Wang, Z.; Duncan, S. C. Org. Lett. 2003, 5, 407. |
| [6] | (d) Doyle, M. P.; Phillips, I. M. Tetrahedron Lett. 2001, 42, 3155. |
| [6] | (e) Doyle, M. P.; Van Oeveren, A.; Westrum, L. J.; Protopopova, M. N.; Clayton, T. W. J. Am. Chem. Soc. 1991, 113, 8982. |
| [7] | For selected examples on Hashimoto’s work, see: (a) Natori, Y.; Anada, M.; Nakamura, S.; Nambu, H.; Hashimoto, S. Heterocycles 2006, 70, 635. |
| [7] | (b) Hashimoto, S.-i.; Watanabe, N.; Sato, T.; Shiro, M.; Ikegami, S. Tetrahedron Lett. 1993, 34, 5109. |
| [7] | (c) Hashimoto, S.-i.; Watanabe, N.; Ikegami, S. Tetrahedron Lett. 1990, 31, 5173. |
| [8] | For selected examples on asymmetric C—H insertion reactions of diazo compounds, see: (a) Li, N.; Yang, X.; Zhu, Y.; Wang, F.; Gong, J; Song, M. Chin. Chem. Lett. 2022, 33, 2437. |
| [8] | (b) Fu, J.; Ren, Z.; Bacsa, J.; Musaev, D. G.; Davies, H. M. L. Nature 2018, 564, 395. |
| [8] | (c) Liao, K.; Negretti, S.; Musaev, D. G.; Bacsa, J.; Davies, H. M. L. Nature 2016, 533, 230. |
| [8] | (d) Davies, H. M. L.; Hansen, T.; Churchill, M. R. J. Am. Chem. Soc. 2000, 122, 3063. |
| [9] | Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, D. A.; van Basten, A. J. Am. Chem. Soc. 1994, 116, 4507. |
| [10] | Miyazawa, T.; Minami, K.; Ito, M.; Anada, M.; Matsunaga, S.; Hashimoto, S. Tetrahedron 2016, 72, 3939. |
| [11] | Buckley, A. M.; Crowley, D. C.; Brouder, T. A.; Ford, A.; Khandavilli, U. B. R.; Lawrence, S. E.; Maguire, A. R. ChemCatChem 2021, 13, 4318. |
| [12] | Zhang, X.; Li, Z.; Chu, J. C. K.; Chiu, P. Tetrahedron Lett. 2011, 52, 6763. |
| [13] | Clarke, L. A.; Ring, A.; Ford, A.; Sinha, A. S.; Lawrence, S. E.; Maguire, A. R. Org. Biomol. Chem. 2014, 12, 7612. |
| [14] | Brouder, T. A.; Slattery, C. N.; Ford, A.; Khandavilli, U. B. R.; Skořepová, E.; Eccles, K. S.; Lusi, M.; Lawrence, S. E.; Maguire, A. R. J. Org. Chem. 2019, 84, 7543. |
| [15] | For selected examples on transition-metal catalyzed Buchner reactions, see: (a) Crowley, D. C.; Lynch D.; Maguire, A. R. J. Org. Chem. 2018, 83, 3794. |
| [15] | (b) Fleming, G. S.; Beeler, A. B. Org. Lett. 2017, 19, 5268. |
| [15] | (c) McNamara, O. A.; Buckley, N. R.; O'Leary, P.; Harrington, F.; Kelly, N.; O'Keeffe, S.; Stack, A.; O'Neill, S.; Lawrence, S. E.; Slattery, C. N.; Maguire, A. R. Org. Lett. 2017, 19, 5268. |
| [15] | (d) Slattery, C. N.; Clarke, L.-A.; O'Neill, S.; Ring, A.; Forda, A.; Maguire, A. R. Synlett 2012, 765. |
| [15] | (e) Kane, J. L.; Shea, K. M.; Crombie, A. L.; Danheiser, R. L. Org. Lett. 2011, 13, 1081. |
| [15] | (f) O'Neill, S.; O'Keeffe, S.; Harrington, F.; Maguire, A. R. Synlett 2009, 2312. |
| [15] | (g) O'Keeffe, S.; Harrington, F.; Maguire, A. R. Synlett. 2007, 2367. |
| [15] | (h) Maguire, A. R.; O'Leary, P.; Harrington, F.; Lawrence, S. E.; Blake, A. J. J. Org. Chem. 2001, 66, 7166. |
| [15] | (i) Doyle, M. P.; Phillips, I. M. Tetrahedron Lett. 2001, 42, 3155. |
| [15] | (j) Doyle, M. P.; Hu, W.; Timmons, D. J. Org. Lett. 2001, 3, 933. |
| [15] | (k) Merlic, C. A.; Zechman, A. L.; Miller, M. M. J. Am. Chem. Soc. 2001, 123, 11101. |
| [15] | (l) Cordi, A. A.; Lacoste, J. M.; Hennig, P. J. Chem. Soc., Perkin Trans. 1 1993, 3. |
| [15] | (m) Padwa, A.; Austin, D. J.; Price, A. T.; Semones, M. A.; Doyle, M. P.; Protopopova, M. N.; Winchester, W. R.; Tran, A. J. Am. Chem. Soc. 1993, 115,8669. |
| [15] | (n) Doyle, M. P.; Ene, D. G.; Forbes, D. C.; Pillow, T. H. Chem. Commun. 1999, 1691. |
| [15] | (o) Duddeck, H.; Kennedy, M.; Mckervey, M. A.; Twohig, F. M. J. Chem. Soc., Chem. Commun. 1988, 24, 1586. |
| [15] | (p) Buchner, E.; Curtius, T. Ber. Dtsch. Chem. 1885, 18, 2377. |
| [16] | Liu, Y.; Deng, Y.; Zavalij, P. Y.; Liu, R.; Doyle, M. P. Chem. Commun. 2015, 51, 565. |
| [17] | Thanh, N. P. T.; Tone, M.; Inoue, H.; Fujisawa, I.; Iwasa, S. Chem. Commun. 2019, 55, 13398. |
| [18] | For selected reviews on transition-metal catalyzed enantioselective Si—H insertion reactions, see: (a) Keipour, H.; Keipour, V.; Ollevier, T. Org. Biomol. Chem. 2017, 15, 5441. |
| [18] | (b) Gurmessa, G. T.; Singh, G. S. Res. Chem. Intermed. 2017, 43, 6447. |
| [18] | (c) Gillingham, D.; Fei, N. Chem. Soc. Rev. 2013, 42, 4918. |
| [18] | (d) Zhu, S.-F.; Zhou, Q.-L. Acc. Chem. Res. 2012, 45, 1365. |
| [19] | Zhang, X.; Fang, J.; Zhu, Y.; Cai, C.; Lu, G. Chin. Chem. Lett. 2021, 32, 1280. |
| [20] | Yasutomi, Y.; Suematsu, H.; Katsuki, T. J. Am. Chem. Soc. 2010, 132, 4510. |
| [21] | Nakagawa, Y.; Chanthamath, S.; Fujisawa, I.; Shibatomi, K.; Iwasa, S. Chem. Commun. 2017, 53, 3753. |
| [22] | Jagannathan, J. R.; Fettinger, J. C.; Shaw, J. T.; Franz, A. K. J. Am. Chem. Soc. 2020, 142, 11674. |
| [23] | (a) Zu, B.; Guo, Y.; He, C. J. Am. Chem. Soc. 2021, 143, 16302. |
| [23] | (b) Yang, J.; Zhang, J.-W.; Bao, W.; Qiu, S.-Q.; Li, S.; Xiang, S.-H.; Song, J.; Zhang, J.; Tan, B. J. Am. Chem. Soc. 2021, 143, 12924. |
| [23] | (c) Yang, K.; Mao, Y.; Xu, J.; Wan, H.; He, Y.; Li, W.; Song, Q. J. Am. Chem. Soc. 2021, 143, 10048. |
| [24] | Zhang, G.; Zhang, Z.; Hou, M.; Cai, X.; Yang, K.; Yu, P.; Song, Q. Nat. Commun. 2022, 13, 2624. |
/
| 〈 |
|
〉 |