STEREOSPECIFIC DEHYDRATIVE ALKYLATION OF BIS-SULFONES - SYNTHESIS OF A LESSER TEA TORTRIX PHEROMONE(1)

被引:47
作者
YU, JR [1 ]
CHO, HS [1 ]
FALCK, JR [1 ]
机构
[1] UNIV TEXAS,SW MED CTR,DEPT PHARMACOL,DALLAS,TX 75235
关键词
D O I
10.1021/jo00074a010
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The intra- and intermolecular condensation of alcohols with bis-sulfone methylenes, i.e., dehydrative alkylation, using DEAD and Ph3P proceeds stereospecifically at room temperature under essentially neutral conditions affording good to excellent yields of alkylation/annulation products.
引用
收藏
页码:5892 / 5894
页数:3
相关论文
共 26 条
[1]   DIRECT, HIGH-YIELD TRANSFORMATION OF TETRAHYDROPYRANYL ETHERS TO ACETATES [J].
BAKOS, T ;
VINCZE, I .
SYNTHETIC COMMUNICATIONS, 1989, 19 (3-4) :523-528
[2]   ORGANIC-SYNTHESIS WITH SULFONES .32. A CONVENIENT ROUTE TO ALPHA,BETA-UNSATURATED SULFONES FROM SATURATED SULFONES [J].
BAUDIN, JB ;
JULIA, M ;
ROLANDO, C ;
VERPEAUX, JN .
TETRAHEDRON LETTERS, 1984, 25 (30) :3203-3204
[3]   MAGNESIUM IN METHANOL - SUBSTITUTE FOR SODIUM AMALGAM IN DESULFONYLATION REACTIONS [J].
BROWN, AC ;
CARPINO, LA .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (10) :1749-1750
[5]   MECHANISM OF THE MITSUNOBU ESTERIFICATION REACTION .1. THE INVOLVEMENT OF PHOSPHORANES AND OXYPHOSPHONIUM SALTS [J].
CAMP, D ;
JENKINS, ID .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3045-3049
[6]  
CASTRO BR, 1983, ORG REACTIONS, V29, P1
[7]   ENANTIOMERICALLY ENRICHED TERT-BOC-PROTECTED ALPHA-AMINOORGANOLITHIUMS - PREPARATION AND CONFIGURATIONAL STABILITY [J].
CHONG, JM ;
PARK, SB .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2220-2222
[8]   A NEW METHOD FOR SILYLATION OF HYDROXYLIC COMPOUNDS - REACTION OF PHENOLS AND ALCOHOLS WITH SILANOLS MEDIATED BY DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE [J].
CLIVE, DLJ ;
KELLNER, D .
TETRAHEDRON LETTERS, 1991, 32 (49) :7159-7160
[9]   ORGANOALKALI COMPOUNDS BY RADICAL-ANION INDUCED REDUCTIVE METALATION OF PHENYL THIOETHERS [J].
COHEN, T ;
BHUPATHY, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (04) :152-161
[10]   SYNTHESIS OF ALKYL NITRONATES VIA MITSUNOBU CONDENSATION [J].
FALCK, JR ;
YU, JR .
TETRAHEDRON LETTERS, 1992, 33 (45) :6723-6726