Uncatalyzed aldol reaction using a dimethylsilyl enolate and α-dimethylsilyl ester in N,N-dimethylformamide

被引：41

作者：

Miura, K ^{[1
]}

Sato, H ^{[1
]}

Tamaki, K ^{[1
]}

Ito, H ^{[1
]}

Hosomi, A ^{[1
]}

机构：

[1] Univ Tsukuba, Dept Chem, Tsukuba, Ibaraki 305, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 17期

关键词：

D O I：

10.1016/S0040-4039(98)00275-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dimethylsilyl enolates and alpha-dimethylsilyl esters reacted with aldehydes in N,N-dimethyl-formamide without an activator to give aldol adducts in moderate to good yields. Under the same conditions, the corresponding trimethylsilyl derivatives exhibited lower reactivities toward the aldol reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2585 / 2588

页数：4

共 24 条

[1] KETENE ALKYLTRIALKYLSILYL ACETALS - SYNTHESIS, PRYOLYSIS AND NMR STUDIES [J].

AINSWORTH, C ;

CHEN, F ;

KUO, YN .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1972, 46 (01) :59-+

[2] INTRAMOLECULAR HYDROSILYLATIONS .2. THE ANTI-SELECTIVE REDUCTION OF BETA-HYDROXYKETONES [J].

ANWAR, S ;

DAVIS, AP .

TETRAHEDRON, 1988, 44 (13) :3761-3770

[3] Chemistry of trichlorosilyl enolates .1. New reagents for catalytic, asymmetric aldol additions [J].

Denmark, SE ;

Winter, SBD ;

Su, XP ;

Wong, KT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (31) :7404-7405

[4] The chemistry of trichlorosilyl enolates .2. Highly-selective asymmetric aldol additions of ketone enolates [J].

Denmark, SE ;

Wong, KT ;

Stavenger, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) :2333-2334

[5] 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

[6] CHEMISTRY OF ENOXYSILACYCLOBUTANES .3. UNCATALYZED, SYN-SELECTIVE, ASYMMETRIC ALDOL ADDITIONS [J].

DENMARK, SE ;

GRIEDEL, BD .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5136-5138

[7] THE CHEMISTRY OF ENOXYSILACYCLOBUTANES - HIGHLY SELECTIVE, UNCATALYZED ALDOL ADDITIONS [J].

DENMARK, SE ;

GRIEDEL, BD ;

COE, DM .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :988-990

[8]

Gennari C., 1991, COMPREHENSIVE ORGANI, V2, P629, DOI DOI 10.1016/B978-0-08-052349-1.00043-3

[9] CATALYSIS OF THE MUKAIYAMA ALDOL REACTION USING CATIONIC ZIRCONOCENE COMPLEXES [J].

HONG, YP ;

NORRIS, DJ ;

COLLINS, S .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (13) :3591-3594

[10] CHEMISTRY OF CARBANIONS .18. PREPARATION OF TRIMETHYLSILYL ENOL ETHERS [J].

HOUSE, HO ;

CZUBA, LJ ;

GALL, M ;

OLMSTEAD, HD .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (08) :2324-&

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