利用硼烷和手性恶唑硼烷催化剂（CBS catalyst）对映异构选择性的还原酮得到相应的手性醇。通常情况下，MeCBS比较常用 (R'' = Me,通过改变取代基可以增加选择性)。

反应机理：

反应机理表明此反应的高对映异构选择性和高反应速率，只受CBS催化剂的影响。次催化剂既作为手性助剂也作为 Lewis 酸参与反应。

最新文献：

Practical enantioselective reduction of ketones using oxazaborolidine catalyst generated in situ from chiral lactam alcohol and borane
Y. Kawanami, S. Murao, T. Ohga, N. Kobayashi, Tetrahedron, 2003, 59, 8411-8414.

An Efficient and Catalytically Enantioselective Route to (S)-(-)-Phenyloxirane
E. J. Corey, S. Shibata, R. K. Bakshi, J. Org, Chem., 1988, 53, 2861-2863.

A novel enantioselective synthesis of α-amino acids has been developed, which is broad in scope, simple in application, and advantageous for many α-amino acids of interest in chemistry, biology, medicine.
E. J. Corey, J. O. Link, J. Am. Chem. Soc., 1992, 114, 1906-1908.

编译自：Organic Chemistry Portal

相关介绍

Corey–Bakshi–Shibata (CBS)试剂是一种由脯氨酸制备而来的手性催化剂。又被称为Corey恶唑硼烷 ，可以和硼烷共用对映选择性的还原酮，催化不对称的Diels–Alder反应和 [3 + 2]环加成。

试剂的制备

机理和催化循环

反应实例

参考文献

1. (a) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551–5553.

(b) Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C.-P.; Singh, V. K. J. Am. Chem.Soc. 1987, 109, 7925–7926. (c) Corey, E. J.; Shibata, S.; Bakshi, R. K. J. Org. Chem.1988, 53, 2861–2863.

2. Reviews: (a) Corey, E. J. Pure Appl. Chem. 1990, 62, 1209–1216. (b) Wallbaum, S.;Martens, J. Tetrahedron: Asymm. 1992, 3, 1475–1504. (c) Singh, V. K. Synthesis 1992, 605–617. (d) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763–784. (e) Taraba, M.; Palecek, J. Chem. Listy 1997, 91, 9–22. (f) Corey, E. J.; Helal, C. J.Angew. Chem. Int. Ed. 1998, 37, 1986–2012. g) Corey, E. J. Angew. Chem. Int. Ed. 2002, 41, 1650–1667. (h) Itsuno, S. Org. React. 1998, 52, 395–576. (i) Cho, B. T. Aldrichimica Acta 2002, 35, 3–16. (j) Glushkov, V. A.; Tolstikov, A. G. Russ. Chem. Rev. 2004, 73, 581–608. (k) Cho, B .T. Tetrahedron 2006, 62, 7621–7643.

3. (a) Mathre, D. J.; Thompson, A. S.; Douglas, A. W.; Hoogsteen, K.; Carroll, J. D.; Corley, E. G.; Grabowski, E. J. J. J. Org. Chem. 1993, 58, 2880–2888. (b) Xavier, L.C.; Mohan, J. J.; Mathre, D. J.; Thompson, A. S.; Carroll, J. D.; Corley, E. G.; Desmond,R. Org. Synth. 1997, 74, 50–71.

4. Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1996, 37, 4837–4840.

5. Clark, W. M.; Tickner-Eldridge, A. M.; Huang, G. K.; Pridgen, L. N.; Olsen, M. A.;Mills, R. J.; Lantos, I.; Baine, N. H. J. Am. Chem. Soc. 1998, 120, 4550–4551.

6. Cho, B. T.; Kim, D. J. Tetrahedron: Asymmetry 2001, 12, 2043–2047.

7. Price, M. D.; Sui, J. K.; Kurth, M. J.; Schore, N. E. J. Org. Chem. 2002, 67, 8086–8089.

8. Degni, S.; Wilen, C.-E.; Rosling, A. Tetrahedron: Asymmetry 2004, 15, 1495–1499.

9. Watanabe, H.; Iwamoto, M.; Nakada, M. J. Org. Chem. 2005, 70, 4652–4658.

10. Zhou, G.; Corey, E. J. J. Am. Chem. Soc. 2005, 127, 11958–11959.

11. Yeung, Y.-Y.; Hong, S.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 6310–6311.

12. Patti, A.; Pedotti, S. Tetrahedron: Asymmetry 2008, 19, 1891–1897.

13. Sridhar, Y.; Srihari, P. Eur. J. Org. Chem. 2013, 578–587.

编译自：J.J. Li, Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications,  Corey–Bakshi–Shibata (CBS) reagent，page 168-169.