HIGHLY ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF BETA-AMINO ACID-ESTERS AND BETA-LACTAMS FROM ACHIRAL ESTERS AND IMINES

被引：112

作者：

COREY, EJ

DECICCO, CP

NEWBOLD, RC

机构：

[1] Department of Chemistry, Harvard University, Cambridge

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 39期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(00)92366-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of S-tert-butyl thiopropionate with a number of N-benzyl or N-allyl aldimines (4) as promoted by the chiral diazaborolidine 1 and triethylamine afforded the beta-amino acid esters 5 with high diastereoselectivity and enantioselectivity, providing a simple route to chiral beta-lactams 6.

引用

页码：5287 / 5290

页数：4

共 22 条

[1] STEREOCONTROLLED TOTAL SYNTHESIS OF THE CHIRAL BUILDING BLOCK (3S,4R)-3-[(R)-1-HYDROXYETHYL]-4-ACETYLOXY-AZETIDIN-2-ONE - A USEFUL SYNTHON FOR THE SYNTHESIS OF (+)-THIENAMYCIN, CARBAPENEMS AND PENEMS
CAINELLI, G
CONTENTO, M
GIACOMINI, D
PANUNZIO, M
[J]. TETRAHEDRON LETTERS, 1985, 26 (07) : 937 - 940
[2] HIGHLY ENANTIOSELECTIVE AND DIASTEREOSELECTIVE IRELAND-CLAISEN REARRANGEMENT OF ACHIRAL ALLYLIC ESTERS
COREY, EJ
LEE, DH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (10) : 4026 - 4028
[3] A PRACTICAL AND GENERAL ENANTIOSELECTIVE SYNTHESIS OF CHIRAL PROPA-1,2-DIENYL AND PROPARGYL CARBINOLS
COREY, EJ
YU, CM
LEE, DH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) : 878 - 879
[4] PRACTICAL ENANTIOSELECTIVE DIELS-ALDER AND ALDOL REACTIONS USING A NEW CHIRAL CONTROLLER SYSTEM
COREY, EJ
IMWINKELRIED, R
PIKUL, S
XIANG, YB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) : 5493 - 5495
[5] A PRACTICAL AND EFFICIENT METHOD FOR ENANTIOSELECTIVE ALLYLATION OF ALDEHYDES
COREY, EJ
YU, CM
KIM, SS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) : 5495 - 5496
[6] ENANTIOSELECTIVE VICINAL HYDROXYLATION OF TERMINAL AND E-1,2-DISUBSTITUTED OLEFINS BY A CHIRAL COMPLEX OF OSMIUM TETRAOXIDE - AN EFFECTIVE CONTROLLER SYSTEM AND A RATIONAL MECHANISTIC MODEL
COREY, EJ
JARDINE, PD
VIRGIL, S
YUEN, PW
CONNELL, RD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) : 9243 - 9244
[7] NEW ENANTIOSELECTIVE ROUTES TO BIOLOGICALLY INTERESTING COMPOUNDS
COREY, EJ
[J]. PURE AND APPLIED CHEMISTRY, 1990, 62 (07) : 1209 - 1216
[8] VERSATILE CHIRAL REAGENT FOR THE HIGHLY ENANTIOSELECTIVE SYNTHESIS OF EITHER ANTI OR SYN ESTER ALDOLS
COREY, EJ
KIM, SS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) : 4976 - 4977
[9] COREY EJ, IN PRESS TETRAHEDRON
[10] STEREOSELECTIVE SYNTHESIS OF 3-(1-HYDROXYETHYL)-2-AZETIDINONES FROM 3-HYDROXYBUTYRATES
GEORG, GI
[J]. TETRAHEDRON LETTERS, 1984, 25 (35) : 3779 - 3782

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