SINGLE ELECTRON-TRANSFER IN THE ADDITION OF CHIRAL DIPOLE-STABILIZED ORGANOLITHIUMS TO CARBONYLS - STEREOCHEMISTRY OF A CHIRAL NUCLEOPHILE AS A MECHANISTIC PROBE

被引:23
作者
REIN, KS [1 ]
CHEN, ZH [1 ]
PERUMAL, PT [1 ]
ECHEGOYEN, L [1 ]
GAWLEY, RE [1 ]
机构
[1] UNIV MIAMI,DEPT CHEM,CORAL GABLES,FL 33124
关键词
D O I
10.1016/0040-4039(91)85007-R
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Spectroscopic and stereochemical evidence is provided which suggests that single electron transfer (SET) accounts for the difference in selectivity observed in the reaction of metalated pivalamides and oxazolines with carbonyls.
引用
收藏
页码:1941 / 1944
页数:4
相关论文
共 25 条
[1]   VOLTAMMETRY IN SULFOLANE - ELECTROCHEMICAL BEHAVIOR OF BENZALDEHYDE AND SUBSTITUTED BENZALDEHYDES [J].
ARMSTRONG, NR ;
QUINN, RK ;
VANDERBORGH, NE .
ANALYTICAL CHEMISTRY, 1974, 46 (12) :1759-1764
[2]   STEREOCHEMISTRY OF LITHIATION OF N-METHYLFORMAMIDE - A THEORETICAL-STUDY [J].
BACH, RD ;
BRADEN, ML ;
WOLBER, GJ .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (09) :1509-1514
[3]   ON THE RELATIVE ENERGIES OF ABINITIO STRUCTURES OF N-METHYLFORMAMIDE ANIONS AND THEIR LITHIUM DERIVATIVES - AN ESTIMATE OF THE MAGNITUDE OF CHELATE STABILIZATION [J].
BARTOLOTTI, LJ ;
GAWLEY, RE .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12) :2980-2982
[4]   DIPOLE-STABILIZED CARBANIONS - NOVEL AND USEFUL INTERMEDIATES [J].
BEAK, P ;
REITZ, DB .
CHEMICAL REVIEWS, 1978, 78 (03) :275-316
[5]   METALATION AND ELECTROPHILIC SUBSTITUTION OF AMINE DERIVATIVES ADJACENT TO NITROGEN - ALPHA-METALLO AMINE SYNTHETIC EQUIVALENTS [J].
BEAK, P ;
ZAJDEL, WJ ;
REITZ, DB .
CHEMICAL REVIEWS, 1984, 84 (05) :471-523
[6]  
FAULEY JJ, 1971, J ORG CHEM, V36, P3065
[7]   SYNTHESIS OF R-LAUDANOSINE AND 9-R-O-METHYLFLAVINANTINE BY ASYMMETRIC ALKYLATION [J].
GAWLEY, RE ;
SMITH, GA .
TETRAHEDRON LETTERS, 1988, 29 (03) :301-302
[8]   CHIRAL DIPOLE-STABILIZED ANIONS - EXPERIMENT AND THEORY IN NONBENZYLIC SYSTEMS - 100-PERCENT STEREOSELECTIVE DEPROTONATION AND 2-ELECTRON VS SINGLE-ELECTRON TRANSFER IN THE CHEMISTRY OF LITHIUM AND COPPER PIPERIDINOOXAZOLINES [J].
GAWLEY, RE ;
HART, GC ;
BARTOLOTTI, LJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (01) :175-181
[9]  
GAWLEY RE, 1991, COMP ORG SYN, V3
[10]  
GAWLEY RE, 1991, COMP ORG SYN, V1