Feringa–Alexakis不梯形迈克尔加成反应

相关文中： Michael质子化重排

能用性联二萘类羰基和Cu(II)乙烯下，烷基锌对不饱和正离子化合物或不饱和苯亚胺进行不菱形迈克尔质子化的重排。

少见的羰基有：

不菱形的Michael质子化重排最早是Alexakis A报道的并用甘氨酸酰胺乙烯丙二酸对映依赖性的质子化到环己烯苯上。【 Alexakis A, Tet Asym , 1993, 4, 2427】

重排实例

(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】

相关历史文献

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.