Highly enantioselective Cr(salen)-catalyzed Mukaiyama Aldol reaction:: Construction of δ-hydroxy-β-keto ester derivatives

被引：19

作者：

Shimada, Y ^{[1
]}

Matsuoka, Y ^{[1
]}

Irie, R ^{[1
]}

Katsuki, T ^{[1
]}

机构：

[1] Kyushu Univ, Dept Chem, Fac Sci,Grad Sch, Higashi Ku, Fukuoka 8128581, Japan

来源：

SYNLETT | 2004年 / 01期

关键词：

Mukaiyama aldol reaction; asymmetric catalysis; Cr(salen); delta-hydroxy-beta-keto ester;

D O I：

10.1055/s-2003-43351

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mukaiyama aldol reactions of silyl dienol ether and aldehydes proceeded with high enantioselectivity to give delta-hydroxy-beta-keto ester derivatives by using chiral cationic Cr(salen) complex as catalyst in the presence of isopropyl alcohol and base (triethylamine or 2,6-dimethylpyridine).

引用

页码：57 / 60

页数：4

共 22 条

[1] Asymmetric hetero Diels-Alder reaction using chiral cationic metallosalen complexes as catalysts [J].

Aikawa, K ;

Irie, R ;

Katsuki, T .

TETRAHEDRON, 2001, 57 (05) :845-851

[2]

CARREIRA EM, 1999, COMPREHENSIVE ASYMME, V3, P997

[3] Asymmetric auto-inductive aldol reaction by self-assembly of chiral ligands [J].

De Rosa, M ;

Acocella, MR ;

Soriente, A ;

Scettri, A .

TETRAHEDRON-ASYMMETRY, 2001, 12 (10) :1529-1531

[4] Enantioselective and diastereoselective mukaiyama-Michael reactions catalyzed by bis(oxazoline) Copper(II) complexes [J].

Evans, DA ;

Scheidt, KA ;

Johnston, JN ;

Willis, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (19) :4480-4491

[5] C-2-symmetric copper(II) complexes as chiral Lewis acids. Catalytic enantioselective aldol additions of silylketene acetals to (benzyloxy)acetaldehyde [J].

Evans, DA ;

Murry, JA ;

Kozlowski, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (24) :5814-5815

[6] Platinum-catalyzed enantioselective aldol addition of ketene silyl acetals to aldehydes [J].

Fujimura, O .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (39) :10032-10039

[7] Catalytic asymmetric aldol reactions in aqueous media using chiral bis-pyridino-18-crown-6-rare earth metal triflate complexes [J].

Hamada, T ;

Manabe, K ;

Ishikawa, S ;

Nagayama, S ;

Shiro, M ;

Kobayashi, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (10) :2989-2996

[8]

Kitajima H, 1997, SYNLETT, P568

[9] Catalytic asymmetric Mukaiyama aldol reactions in aqueous media [J].

Kobayashi, S ;

Nagayama, S ;

Busujima, T .

TETRAHEDRON, 1999, 55 (29) :8739-8746

[10] CATALYTIC ASYMMETRIC ALDOL REACTION OF THE SILYL ENOL ETHER OF ACETIC-ACID THIOESTER WITH ALDEHYDES USING CHIRAL TIN(II) LEWIS ACID [J].

KOBAYASHI, S ;

FURUYA, M ;

OHTSUBO, A ;

MUKAIYAMA, T .

TETRAHEDRON-ASYMMETRY, 1991, 2 (07) :635-638

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