STEREOSELECTIVE ALKYLATIONS OF CHIRAL, PHOSPHORUS-STABILIZED BENZYLIC CARBANIONS

被引:62
作者
DENMARK, SE
DOROW, RL
机构
[1] Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana
关键词
D O I
10.1021/jo00311a003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
: A series of 6-substituted 2-benzyl-3-tert-bu-tyl-1,3,2-oxazaphosphorinanes was prepared in racemic and enantiomerically pure form. The diastereoselectivity of alkylation of the derived anions was examined as a function of ring substitution pattern, base, solvent, electrophile, and enantiomeric composition. © 1990, American Chemical Society. All rights reserved.
引用
收藏
页码:5926 / 5928
页数:3
相关论文
共 37 条
[1]   3-METALATED ENAMINES .10. FORMATION AND REACTIVITY OF 1-(DIETHOXYPHOSPHORYL)-1-(DIMETHYLAMINO)ALLYL ANIONS [J].
AHLBRECHT, H ;
FARNUNG, W .
CHEMISCHE BERICHTE-RECUEIL, 1984, 117 (01) :1-22
[2]   DIASTEREOSELECTIVITY IN THE ALKYLATION OF CHIRAL 2-AMINOMETHYL-1,3,2-DIOXAPHOSPHORINANE 2-OXIDES [J].
BARTLETT, PA ;
MCLAREN, KL .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1987, 33 (1-2) :1-14
[3]   EXPEDIENT AND HIGH-YIELD SYNTHESIS OF ALKYLPHOSPHONYL DICHLORIDES UNDER MILD, NEUTRAL CONDITIONS - REACTION OF BIS(TRIMETHYLSILYL)ALKYL PHOSPHONATES WITH OXALYL CHLORIDE DIMETHYLFORMAMIDE [J].
BHONGLE, NN ;
NOTTER, RH ;
TURCOTTE, JG .
SYNTHETIC COMMUNICATIONS, 1987, 17 (09) :1071-1076
[4]  
Biellmann J.-F., 1982, ORG REACT NY, V27, P180
[5]   STRUCTURAL STUDIES OF CARBANIONIC SPECIES FORMED FROM PHOSPHONATES - ANIONS OF DIETHYL BENZYL-PHOSPHONATES AND CYANOMETHYLPHOSPHONATES [J].
BOTTINSTRZALKO, T ;
SEYDENPENNE, J ;
POUET, MJ ;
SIMONNIN, MP .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (22) :4346-4351
[6]   SYNTHESIS OF OLEFINS FROM BETA-HYDROXYPHOSPHONAMIDES - STEREOCHEMISTRY AND EXTENSION TO FORMATION OF CONJUGATED DIENES [J].
COREY, EJ ;
CANE, DE .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (10) :3053-&
[8]  
CORSET J, 1988, PURE APPL CHEM, P238
[9]  
CRAMER C, UNPUB
[10]  
Denmark S. E., UNPUB