CONFIGURATIONALLY FIXED ALPHA-ALKOXYORGANOCOPPER REAGENTS - 1,4-ADDITION OF CYCLIC ENANTIOPURE TRANSFERABLE LIGANDS WITH COMPLETE RETENTION OF CONFIGURATION

被引:47
作者
LINDERMAN, RJ
GRIEDEL, BD
机构
[1] Department of Chemistry, North Carolina State University, Raleigh
关键词
D O I
10.1021/jo00019a002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Optically active 4-lithio-1,3-dioxanes have been converted to the corresponding TMEDA-organocopper reagents and shown to undergo conjugate addition reactions to ethyl propiolate with complete retention of configuration.
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页码:5491 / 5493
页数:3
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共 19 条
[1]  
CHONG JM, 1990, TETRAHEDRON LETT, V31, P1985
[2]   A GENERAL PREPARATIVE METHOD FOR ALPHA-LITHIOETHERS AND ITS APPLICATION TO A CONCISE, PRACTICAL SYNTHESIS OF BREVICOMIN [J].
COHEN, T ;
MATZ, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (22) :6900-6902
[4]   ENANTIOSPECIFIC SYNTHESIS OF (+)-(6S,8R,E)-METHYL 2,3-DIDEHYDRONONACTATE [J].
DESCHENAUX, PF ;
JACOTGUILLARMOD, A .
HELVETICA CHIMICA ACTA, 1990, 73 (07) :1861-1864
[5]  
FONT J, 1984, J HETEROCYCLIC CHEM, V21, P327
[6]  
FUCHS PL, 1987, J AM CHEM SOC, V109, P4930
[7]   TRIMETHYLSILYL CHLORIDE TETRAMETHYLETHYLENEDIAMINE FACILITATED ADDITIONS OF ORGANOCOPPER REAGENTS (RCU) TO ENONES [J].
JOHNSON, CR ;
MARREN, TJ .
TETRAHEDRON LETTERS, 1987, 28 (01) :27-30
[8]  
KISHI Y, 1983, J ORG CHEM, V48, P3833
[9]   HIGHLY SELECTIVE SYN ACYCLIC HOMOALDOL CHEMISTRY - SYNTHESIS OF CIS-3,4-DISUBSTITUTED BUTYROLACTONES [J].
LINDERMAN, RJ ;
MCKENZIE, JR .
TETRAHEDRON LETTERS, 1988, 29 (32) :3911-3914
[10]   A NOVEL SYNTHESIS OF TETRAHYDROFURANS VIA A SYNTHETIC EQUIVALENT TO A CARBONYL YLIDE [J].
LINDERMAN, RJ ;
GODFREY, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (18) :6249-6251