THE STEREOSELECTIVE SYNTHESIS OF SUCCINAMIDE DERIVATIVES VIA ENOLATE OXIDATIVE COUPLING

被引:49
作者
PORTER, NA
SU, Q
HARP, JJ
ROSENSTEIN, IJ
MCPHAIL, AT
机构
[1] Department of Chemistry Duke University Durham
关键词
D O I
10.1016/0040-4039(93)88058-Q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enolates derived from optically pure oxazolidines couple with high stereoselectivity when oxidized with iodine or cupric salts.
引用
收藏
页码:4457 / 4460
页数:4
相关论文
共 12 条
[1]   OXIDATIVE COUPLING .2. THE TOTAL SYNTHESIS OF ENTEROLACTONE [J].
BELLETIRE, JL ;
FREMONT, SL .
TETRAHEDRON LETTERS, 1986, 27 (02) :127-130
[2]   OXIDATIVE COUPLING OF CARBOXYLIC-ACID DIANIONS [J].
BELLETIRE, JL ;
SPLETZER, EG ;
PINHAS, AR .
TETRAHEDRON LETTERS, 1984, 25 (52) :5969-5972
[3]  
BELLETIRE JL, 1987, J ORG CHEM, V52, P3745
[4]  
BROCKSOM TJ, 1975, SYNTHESIS-STUTTGART, P396
[5]   ACYCLIC STEREOSELECTION .30. STEREOSELECTION IN THE MICHAEL ADDITION-REACTION .2. STEREOCHEMISTRY OF THE KINETIC MICHAEL REACTION OF AMIDE ENOLATES WITH ENONES [J].
HEATHCOCK, CH ;
HENDERSON, MA ;
OARE, DA ;
SANNER, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (16) :3019-3022
[6]   SYNTHESIS OF OPTICALLY-ACTIVE BETA-LACTAMS BY THE PHOTOLYTIC REACTION OF IMINES WITH OPTICALLY-ACTIVE CHROMIUM CARBENE COMPLEXES [J].
HEGEDUS, LS ;
IMWINKELRIED, R ;
ALARIDSARGENT, M ;
DVORAK, D ;
SATOH, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (03) :1109-1117
[7]  
Ivanoff D., 1935, B SOC CHIM FR, V2, P76, DOI DOI 10.1002/EJOC.201200665
[8]   ORIGINS OF STEREOSELECTIVITY IN RADICAL ADDITIONS - REACTIONS OF ALKENES AND RADICALS BEARING OXAZOLIDINE AND THIAZOLIDINE AMIDE GROUPS [J].
PORTER, NA ;
ROSENSTEIN, IJ ;
BREYER, RA ;
BRUHNKE, JD ;
WU, WX ;
MCPHAIL, AT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (20) :7664-7676
[9]   CONTROL OF STEREOCHEMISTRY IN FREE-RADICAL REACTIONS WITH OXAZOLIDINE AUXILIARIES [J].
PORTER, NA ;
BRUHNKE, JD ;
WU, WX ;
ROSENSTEIN, IJ ;
BREYER, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) :7788-7790
[10]   REACTION OF ESTER ENOLATES WITH COPPER(II) SALTS - SYNTHESIS OF SUBSTITUTED SUCCINATE ESTERS [J].
RATHKE, MW ;
LINDERT, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (18) :4605-&