杏耀国际

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

常见的配体有：

不对称的Michael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.Thecombinedorgac 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 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

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