在手性聯(lián)二萘類配體和Cu(II)催化下，烷基鋅對(duì)不飽和羰基化合物或不飽和酮亞胺進(jìn)行不對(duì)稱邁克爾加成的反應(yīng)。
常見的配體有：
不對(duì)稱的Michael加成反應(yīng)最早是Alexakis A報(bào)道的利用脯氨酸酯催化丙二酸對(duì)映選擇性的加成到環(huán)己烯酮上?！?nbsp;Alexakis A, Tet Asym, 1993, 4, 2427】
反應(yīng)實(shí)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】
相關(guān)文獻(xiàn)
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
編譯自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 152-153.
