在手性联二萘类配体和Cu(II)催化下，烷基锌对不饱和羰基化合物或不饱和酮亚胺进行不对称迈克尔加成的反应。

常见的配体有：

不对称的Michael加成反应最早是Alexakis A报道的利用脯氨酸酯催化丙二酸对映选择性的加成到环己烯酮上。【 Alexakis A, Tet Asym, 1993, 4, 2427】

反应实例

(1Z,3R)-1,3-Diphenyl-N-[(2-pyridyl)sulfonyl]but-1-en-1-amine (4).  A solution of CuTC (3.8mg, 0.02 mmol) and (R,S,S)-5 (10.6 mg, 0.022 mmol) in dry PhMe (1 mL) was stirred at r.t. for 40 min, and a 2-M solution of Me2Zn in PhMe (200 mL, 0.4 mmol) was added. The mixture was quenched with

sat aqNH4Cl,and extracted withDCM.Thecombinedorganic layers were dried (Na2SO4), evaporated and chromatographed (n-hexanes-EA) to afford 4 (65.4 mg, 80%), white solid, mp 45–47 C.

【Carretero JC, J Org Chem, 2005, 70, 7451】

相关文献

1 Alexakis A Tet Asym 1993 4 2427

2* Yamaguchi M Angew Chem Int 1993 32 1176

3* Feringa BL Angew Chem Int 1997 36 2620

4R* Krause N Angew Chem Int 1998 37 283

5* Pfaltz A Synlett 1997 1429

6* Zhang X Angew Chem Int 1999 38 3518

7* Alexakis A Synlett 1999 1811

8* Chan ASC Chem Comm 1999 11

9R* Feringa BL Acc Chem Res 2000 33 346

10R* Pfaltz A Acc Chem Res 2000 33 336

11R* Krause N Synthesis 2001 171

12R* Alexakis A Pure Appl Chem 2002 74 37

13* Carretero JC J Org Chem 2005 70 7451

14* Ishihara K J Org Chem 2006 71 6474

15R* Ding K Pure Appl Chem 2006 78 293

16* Sasai H Tetrahedron 2007 63 6512

17* Alexakis A Chem Eur J 2007 13 3765

18* Alexakis A Angew Chem Int 2007 46 7462

19* Rosini C ARKIVOC 2008 Viii 116

20R* Alexakis A Chem Rev 2008 108 2796

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 152-153.