ASYMMETRIC-SYNTHESIS OF BETA-AMINO ACIDS AND ALPHA-DEUTERATED BETA-AMINO ACIDS VIA CONJUGATE ADDITION OF HOMOCHIRAL AMIDOCUPRATES

被引：0

作者：

SEWALD, N ^{[1
]}

HILLER, KD ^{[1
]}

HELMREICH, B ^{[1
]}

机构：

[1] TECH UNIV MUNICH,INST WASSERGUTE & ABFALLWIRTSCH,D-85747 GARCHING,GERMANY

来源：

LIEBIGS ANNALEN | 1995年 / 05期

关键词：

ASYMMETRIC CONJUGATE ADDITION; ALPHA; BETA-UNSATURATED ESTERS; HOMOCHIRAL AMIDOCUPRATES; BETA-AMINO ACIDS; ALPHA-DEUTERIO BETA-AMINO ACIDS;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Conjugate addition of homochiral amidocuprates based on N-[(R)-1-phenylethyl]trimethylsilylamine or bis[(R)-1-phenylethyl]amine to alpha,beta-unsaturated esters provides an efficient methodology for the asymmetric synthesis of beta-amino acids. Trapping of the intermediate enolate with D2O yields alpha-deuterated beta-amino acids with excellent stereoselectivity.

引用

页码：925 / 928

页数：4

共 19 条

[1] THE RING-OPENING OF AZIRIDINE-2-CARBOXYLATE ESTERS WITH ORGANOMETALLIC REAGENTS
BALDWIN, JE
ADLINGTON, RM
ONEIL, IA
SCHOFIELD, C
SPIVEY, AC
SWEENEY, JB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (23) : 1852 - 1854
[2] BARRETT GC, 1985, CHEM BIOCH AMINO ACI
[3] ASYMMETRIC MICHAEL ADDITIONS OF HOMOCHIRAL MAGNESIUM AMIDES
BUNNAGE, ME
DAVIES, SG
GOODWIN, CJ
WALTERS, IAS
[J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (01) : 35 - 36
[4] AN EXPEDITIOUS ASYMMETRIC-SYNTHESIS OF ALLOPHENYLNORSTATINE
BUNNAGE, ME
DAVIES, SG
GOODWIN, CJ
ICHIHARA, O
[J]. TETRAHEDRON, 1994, 50 (13) : 3975 - 3986
[5] BUNNAGE ME, 1994, TETRAHEDRON-ASYMMETR, V5, P203
[6] ASYMMETRIC-SYNTHESIS OF HOMOCHIRAL SYN-3-PHENYLISOSERINE AND ANTI-3-PHENYLISOSERINE DERIVATIVES - A PRACTICAL STRATEGY FOR THE SYNTHESIS OF THE TAXOL C-13 SIDE-CHAIN
BUNNAGE, ME
DAVIES, SG
GOODWIN, CJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (13): : 1375 - 1376
[7] COLE DC, 1994, TETRAHEDRON, V50, P9517
[8] ORIGINS OF THE HIGH STEREOSELECTIVITY IN THE CONJUGATE ADDITION OF LITHIUM(ALPHA-METHYLBENZYL)BENZYLAMIDE TO T-BUTYL CINNAMATE
COSTELLO, JF
DAVIES, SG
ICHIHARA, O
[J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (10) : 1999 - 2008
[9] ASYMMETRIC SYNTHESES OF BETA-PHENYLALANINE, ALPHA-METHYL-BETA-PHENYLALANINES AND DERIVATIVES
DAVIES, SG
GARRIDO, NM
ICHIHARA, O
WALTERS, IAS
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (14) : 1153 - 1155
[10] ASYMMETRIC-SYNTHESIS OF R-BETA-AMINO BUTANOIC ACID AND S-BETA-TYROSINE - HOMOCHIRAL LITHIUM AMIDE EQUIVALENTS FOR MICHAEL ADDITIONS TO ALPHA,BETA-UNSATURATED ESTERS
DAVIES, SG
ICHIHARA, O
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (03) : 183 - 186

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