Lithium pyrrolidone catalyzed aldol reaction between aldehyde and trimethylsilyl enolate

被引：40

作者：

Fujisawa, H ^{[1
]}

Mukaiyama, T ^{[1
]}

机构：

[1] Kitasato Inst, Ctr Basic Res, TCI, Kita Ku, Tokyo 1140003, Japan

来源：

CHEMISTRY LETTERS | 2002年 / 08期

关键词：

D O I：

10.1246/cl.2002.858

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Lithium pyrrolidone catalyzed aldol reaction between trimethylsilyl enolates and aldehydes proceeded smoothly in a DMF or pyridine solvent to afford the corresponding aldols under weakly basic conditions.

引用

页码：858 / 859

页数：2

共 22 条

[1] EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION [J].

BORDWELL, FG .

ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (12) :456-463

[2] EQUILIBRIA INVOLVING ORGANIC-ANIONS IN DIMETHYLSULFOXIDE AND N-METHYLPYRROLIDIN-2-ONE - ACIDITIES, ION-PAIRING, AND HYDROGEN-BONDING [J].

BORDWELL, FG ;

BRANCA, JC ;

HUGHES, DL ;

OLMSTEAD, WN .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (16) :3305-3313

[3] CHEMISTRY OF ENOXYSILACYCLOBUTANES - HIGHLY SELECTIVE UNCATALYZED ALDOL ADDITIONS [J].

DENMARK, SE ;

GRIEDEL, BD ;

COE, DM ;

SCHNUTE, ME .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (16) :7026-7043

[4] Asymmetric catalysis of aldol reactions with chiral Lewis bases [J].

Denmark, SE ;

Stavenger, RA .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :432-440

[5] 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

[6] A catalytic aldol reaction between ketene silyl acetals and aldehydes promoted by lithium amide under non-acidic conditions [J].

Fujisawa, H ;

Mukaiyama, T .

CHEMISTRY LETTERS, 2002, (02) :182-183

[7] Magnesium bromide diethyl etherate mediated highly diastereoselective aldol reaction between an aldehyde and a silyl enol ether [J].

Fujisawa, H ;

Sasaki, Y ;

Mukaiyama, T .

CHEMISTRY LETTERS, 2001, (03) :190-191

[8] Spontaneous aldol and Michael additions of simple enoxytrimethylsilanes in DMSO [J].

Génisson, Y ;

Gorrichon, L .

TETRAHEDRON LETTERS, 2000, 41 (25) :4881-4884

[9] CHEMISTRY OF CARBANIONS .23. USE OF METAL-COMPLEXES TO CONTROL ALDOL CONDENSATION [J].

HOUSE, HO ;

CRUMRINE, DS ;

TERANISH.AY ;

OLMSTEAD, HD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (10) :3310-3324

[10] Apparent catalytic generation of chiral metal enolates:: Enantioselective dienolate additions to aldehydes mediated by Tol-BINAP•Cu(II) fluoride complexes [J].

Krüger, J ;

Carreira, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (04) :837-838

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