Enantioselective Michael reaction of malonates and chalcones by phase-transfer catalysis using chiral quaternary ammonium salt

被引：148

作者：

Kim, DY ^{[1
]}

Huh, SC ^{[1
]}

Kim, SM ^{[1
]}

机构：

[1] Soonchunhyang Univ, Dept Chem, Chungnam 336600, South Korea

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 36期

关键词：

phase transfer; Michael reactions; ammonium salt; asymmetric reactions;

D O I：

10.1016/S0040-4039(01)01237-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic enantioselective Michael reaction promoted by quaternary ammonium salt from cinchonidine as a phase-transfer catalyst is described. Treatment of malonate with chalcone derivatives under mild reaction conditions afforded the corresponding Michael adducts in good yields with good to moderate enantiomeric excesses. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6299 / 6301

页数：3

共 44 条

[31]

PATROCINIO VL, 1994, SYNTHESIS-STUTTGART, P474

[32]

Perlmutter P., 1992, CONJUGATE ADDITION R

[33] Enantioselective synthesis of both enantiomers of methyl dihydrojasmonate using solid-liquid asymmetric phase-transfer catalysis [J].

Perrard, T ;

Plaquevent, JC ;

Desmurs, JR ;

Hébrault, D .

ORGANIC LETTERS, 2000, 2 (19) :2959-2962

[34] ASYMMETRIC CONJUGATE ADDITION [J].

ROSSITER, BE ;

SWINGLE, NM .

CHEMICAL REVIEWS, 1992, 92 (05) :771-806

[35] CATALYTIC ASYMMETRIC-SYNTHESIS WITH TRANSCHELATING CHIRAL DIPHOSPHINE LIGAND TRAP - RHODIUM-CATALYZED ASYMMETRIC MICHAEL ADDITION OF ALPHA-CYANO CARBOXYLATES [J].

SAWAMURA, M ;

HAMASHIMA, H ;

ITO, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) :8295-8296

[36] STEREOCHEMISTRY OF ALKYLATION OF ALPHA-LITHIOPIPERIDINES - DIFFERING EFFECTS OF FORMAMIDINE AND URETHANE ACTIVATING GROUPS [J].

SHAWE, TT ;

MEYERS, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2751-2755

[37] Catalytic asymmetric synthesis of tubifolidine [J].

Shimizu, S ;

Ohori, K ;

Arai, T ;

Sasai, H ;

Shibasaki, M .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7547-7551

[38]

Shioiri T., 1997, HDB PHASE TRANSFER C

[39]

Starks C.M., 1994, Phase-Transfer Catalysis: Fundamentals, Applications, and Industrial Perspectives

[40] A new polymer-anchored chiral catalyst for asymmetric Michael addition reactions [J].

Sundararajan, G ;

Prabagaran, N .

ORGANIC LETTERS, 2001, 3 (03) :389-392

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