Sharpless不对称胺基羟基化反应

在锇催化下胺基和羟基对烯烃进行顺式加成，通过加入手性配体（二氢奎宁或二氢奎宁衍生物类手性配体）实现对映选择性。常见的氮源（X􀀐NClNa）包括：

反应机理：

催化循环（跟更多机理的详细介绍，请回复“Sharpless胺基羟基化反应”，回看往期内容）

反应实例

参考文献

1. (a) Herranz, E.; Sharpless, K. B. J. Org. Chem. 1978, 43, 2544-􀀐2548. K. Barry

Sharpless (USA, 1941􀀐) shared the Nobel Prize in Chemistry in 2001 with Herbert

William S. Knowles (USA, 1917􀀐) and Ryoji Noyori (Japan, 1938􀀐) for his work on

chirally catalyzed oxidation reactions. (b) Li, G.; Angert, H. H.; Sharpless, K. B.

Angew. Chem. Int. Ed. 1996, 35, 2813􀀐-2817. (c) Rubin, A. E.; Sharpless, K. B.

Angew. Chem. Int. Ed. 1997, 36, 2637􀀐-2640. (d) Kolb, H. C.; Sharpless, K. B. TransitionMet. Org. Synth. 1998, 2, 243-􀀐260. (Review). (e) Thomas, A.; Sharpless, K. B. J.Org. Chem. 1999, 64, 8379-􀀐8385. (f) Gontcharov, A. V.; Liu, H.; Sharpless, K. B.Org. Lett. 1999, 1, 783-􀀐786.

2. Nicolaou, K. C.; Boddy, C. N. C.; Li, H.; Koumbis, A. E.; Hughes, R.; Natarajan, S.; Jain, N. F.; Ramanjulu, J. M.; Braese, S.; Solomon, M. E. Chem. Eur. J. 1999, 5,2602-􀀐2621.

3. Lohr, B.; Orlich, S.; Kunz, H. Synlett 1999, 1139-􀀐1141.

4. Boger, D. L.; Lee, R. J.; Bounaud, P.-Y.; Meier, P. J. Org. Chem. 2000, 65,

6770-􀀐6772.

5. Demko, Z. P.; Bartsch, M.; Sharpless, K. B. Org. Lett. 2000, 2, 2221􀀐-2223.

6. Barta, N. S.; Sidler, D. R.; Somerville, K. B.; Weissman, S. A.; Larsen, R. D.; Reider, P. J. Org. Lett. 2000, 2, 2821-􀀐2824.

7. Bolm, C.; Hildebrand, J. P.; Muñiz, K. In Catalytic Asymmetric Synthesis; 2nd edn., Ojima, I., Ed.; Wiley􀀐VCH: New York, 2000, 399. (Review).

8. Bodkin, J. A.; McLeod, M. D. J. Chem. Soc., Perkin 1 2002, 2733-􀀐2746. (Review).

9. Rahman, N. A.; Landais, Y. Cur. Org. Chem. 2000, 6, 1369-􀀐1395. (Review).

10. Nilov, D.; Reiser, O. Recent Advances on the Sharpless Asymmetric

Aminohydroxylation. In Organic Synthesis Highlights Schmalz, H.-G.; Wirth, T., eds.; Wiley􀀐VCH: Weinheim, Germany 2003, 118-􀀐124. (Review).

11. Bodkin, J. A.; Bacskay, G. B.; McLeod, M. D. Org. Biomol. Chem. 2008, 6,

2544-􀀐2553.

12. Wong, D.; Taylor, C. M. Tetrahedron Lett. 2009, 50, 1273􀀐-1275.

13. Harris, L.; Mee, S. P. H.; Furneaux, R. H.; Gainsford, G. J.; Luxenburger, A. J. Org.Chem. 2011, 76, 358-􀀐372.

14. Kumar, J. N.; Das, B. Tetrahedron Lett. 2013, 54, 3865􀀐-3867.

编译自：Name Reactions （A Collection of Detailed Reaction Mechanisms）, Jie Jack Li, Sharpless asymmetric amino-hydroxylation，page 546-548.