Direct catalytic asymmetric mannich reaction of unmodified ketones:: Cooperative catalysis of an AlLibis(binaphthoxide) complex and La(OTf)3•nH2O

被引：77

作者：

Yamasaki, S ^{[1
]}

Iida, T ^{[1
]}

Shibasaki, M ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

TETRAHEDRON | 1999年 / 55卷 / 29期

关键词：

D O I：

10.1016/S0040-4020(99)00449-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct catalytic asymmetric Mannich reaction of unmodified ketones is described This was achieved by the cooperative catalysis of a heterobimetallic asymmetric complex: AlLibis(binaphthoxide) (ALB) and La(OTf)(3). nH(2)O in the presence of molecular sieves 3A. The association of ALE and La(OTf)(3). H2O was indicated by means of the Laser Desorption/Ionization Time-of-Flight Mass (LDI-TOF MS) spectrum. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：8857 / 8867

页数：11

共 36 条

[1] Regioselective catalytic asymmetric reaction of Horner-Wadsworth-Emmons reagents with enones: The odyssey of chiral aluminum catalysts [J].

Arai, T ;

Sasai, H ;

Yamaguchi, K ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) :441-442

[2] A new multifunctional heterobimetallic asymmetric catalyst for Michael additions and tandem Michael-Aldol reactions [J].

Arai, T ;

Sasai, H ;

Aoe, K ;

Okamura, K ;

Date, T ;

Shibasaki, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01) :104-106

[3] Catalytic asymmetric synthesis of alpha-hydroxy phosphonates using the Al-Li-BINOL complex [J].

Arai, T ;

Bougauchi, M ;

Sasai, H ;

Shibasaki, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) :2926-2927

[4]

Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO

[5]

2-E

[6] Catalytic asymmetric epoxidation of alpha,beta-unsaturated ketones promoted by lanthanoid complexes [J].

Bougauchi, M ;

Watanabe, S ;

Arai, T ;

Sasai, H ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) :2329-2330

[7] HIGHLY ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF BETA-AMINO ACID-ESTERS AND BETA-LACTAMS FROM ACHIRAL ESTERS AND IMINES [J].

COREY, EJ ;

DECICCO, CP ;

NEWBOLD, RC .

TETRAHEDRON LETTERS, 1991, 32 (39) :5287-5290

[8] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[9] Efficient regio- and enantioselective Mannich reactions [J].

Enders, D ;

Ward, D ;

Adam, J ;

Raabe, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (09) :981-984

[10] Catalytic, enantioselective alkylation of α-imino esters using late transition metal phosphine complexes as catalysts [J].

Ferraris, D ;

Young, B ;

Dudding, T ;

Lectka, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) :4548-4549

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