Asymmetric Michael addition reactions using ethyl (S)-4,4-dimethylpyroglutamate as a chiral auxiliary

被引：15

作者：

Ezquerra, J

Prieto, L

Avendaño, C

Martos, JL

de la Cuesta, E

机构：

[1] Ctr Invest Lilly, Alcobenda 28108, Madrid, Spain

[2] Univ Complutense, Dept Quim Organ & Farmaceut, Fac Farm, E-28040 Madrid, Spain

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 08期

关键词：

asymmetric reactions; Michael addition; carboxylic acids and derivatives; stereoselection;

D O I：

10.1016/S0040-4039(98)02648-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ethyl 4,4-dimethylpyroglutamate has been used as a chiral auxiliary for alpha,beta-unsaturated acids in Michael addition reactions. The conjugate addition of Grignard reagents to the amides in the presence of copper iodide, tetramethylene diamine (TMEDA) and trimethylsilyl chloride, proceeded with high yields and excellent stereoselectivities, yielding after hydrolysis enantiomerically pure beta-substituted carboxylic acid derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.

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收藏

页码：1575 / 1578

页数：4

相关论文

共 26 条

[1] STEREOSELECTIVE DOUBLE ALKYLATION OF ETHYL N-BOC-PYROGLUTAMATE [J].

EZQUERRA, J ;

PEDREGAL, C ;

RUBIO, A ;

VAQUERO, JJ ;

MATIA, MP ;

MARTIN, J ;

DIAZ, A ;

NAVIO, JLG ;

DEETER, JB .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) :4327-4331

[2] (S)-ethyl 4,4-dimethyl pyroglutamate as a new 'quat' chiral auxiliary in aldol condensations [J].

Ezquerra, J ;

Rubio, A ;

Martin, J ;

Navio, JLG .

TETRAHEDRON-ASYMMETRY, 1997, 8 (05) :669-671

[3] ASYMMETRIC CONJUGATE ADDITION OF ORGANOMETALLIC REAGENTS TO CHIRAL ALPHA,BETA-UNSATURATED ESTERS [J].

FANG, CL ;

OGAWA, T ;

SUEMUNE, H ;

SAKAI, K .

TETRAHEDRON-ASYMMETRY, 1991, 2 (05) :389-398

[4] PREPARATION AND ABSOLUTE CONFIGURATION OF ENANTIOMERIC 3,4-DIHYDRO-4-METHYLCOUMARINS [J].

GRIMSHAW, J ;

MILLAR, PG .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (17) :2324-&

[5] Lewis acid promoted conjugate addition of vinylmagnesium bromide to chiral alpha,beta-unsaturated N-acyl oxazolidinones [J].

Han, YL ;

Hruby, VJ .

TETRAHEDRON LETTERS, 1997, 38 (42) :7317-7320

[6]

HELMCHEN G, 1985, TETRAHEDRON LETT, V26, P6501

[7] Conformational preference and diastereoselectivity of (S)-N-(alpha,beta-unsaturated carbonyl)-gamma-trityloxymethyl-gamma-butyrolactam [J].

Kanai, M ;

Muraoka, A ;

Tanaka, T ;

Sawada, M ;

Ikota, N ;

Tomioka, K .

TETRAHEDRON LETTERS, 1995, 36 (51) :9349-9352

[8] ALPHA,BETA-UNSATURATED OXAZOLINES, A POWERFUL TOOL IN ASYMMETRIC DIELS-ALDER CYCLOADDITIONS [J].

KOUKLOVSKY, C ;

POUILHES, A ;

LANGLOIS, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (18) :6672-6679

[9] 1,2-ASYMMETRIC CIS INDUCTION AND ITS APPLICATION TO THE ASYMMETRIC-SYNTHESIS OF PRECURSORS OF BETA-BRANCHED UNUSUAL AMINO-ACIDS [J].

LI, G ;

PATEL, D ;

HRUBY, VJ .

TETRAHEDRON LETTERS, 1994, 35 (15) :2301-2304

[10] DIASTEREOSPECIFIC TANDEM MICHAEL-LIKE ADDITION ELECTROPHILIC BROMINATION - A ONE-POT TANDEM ASYMMETRIC-SYNTHESIS OF PRECURSORS OF UNUSUAL AMINO-ACIDS [J].

LI, GG ;

JAROSINSKI, MA ;

HRUBY, VJ .

TETRAHEDRON LETTERS, 1993, 34 (16) :2561-2564