A NEW METHOD FOR THE DEHYDRATION OF BETA-HYDROXY SULFONES - SYNTHESIS OF (E,S)-GAMMA-HYDROXY-ALPHA,BETA-UNSATURATED SULFONES AND (S)-EPSILON-HYDROXY-(E,E)-ALPHA,GAMMA-DIENYL SULFONES

被引：12
作者：
KANG, SK
PARK, YW
KIM, SG
JEON, JH
机构：
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 04期
关键词：
D O I：
10.1039/p19920000405
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Optically active (E,S)-gamma-hydroxy-alpha,beta-unsaturated sulfones and (S)-epsilon-hydroxy-(E,E)-alpha,gamma-dienyl sulfones have been prepared in a one-pot dehydration procedure from beta,gamma-dihydroxy sulfones and delta,epsilon-dihydroxy allyl sulfones, respectively, via an elimination reaction of the corresponding cyclic sulfites or carbonates formed in situ by treatment with thionyl chloride or carbonyldiimidazole.
引用
收藏
页码：405 / 406
页数：2
相关论文
共 10 条
[1]   SYNTHESIS AND CONJUGATE ADDITIONS TO (E)-GAMMA-ALKOXY-ALPHA-SUBSTITUTED-ALPHA-BETA-UNSATURATED SULFONES [J].
ALCARAZ, C ;
CARRETERO, JC ;
DOMINGUEZ, E .
TETRAHEDRON LETTERS, 1991, 32 (10) :1385-1388
[2]  
BACKVALL JE, 1988, J ORG CHEM, V53, P2398
[3]   FACILE SYNTHESIS OF E-GAMMA-HYDROXY-ALPHA,BETA-UNSATURATED SULFONES FROM ALDEHYDES [J].
DOMINGUEZ, E ;
CARRETERO, JC .
TETRAHEDRON LETTERS, 1990, 31 (17) :2487-2490
[4]   SYNTHESES VIA VINYL SULFONES .22. A CHEMODIRECTED, TRIPLY CONVERGENT TOTAL SYNTHESIS OF D-(+)-CARBACYCLIN [J].
HUTCHINSON, DK ;
FUCHS, PL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (15) :4755-4756
[5]   SYNTHESES WITH SULFONE AID .37. SYNTHESIS OF THE 3 PHEROMONES WITH A DOUBLE BOND-Z - Z,8-DDA - Z,9-DDA - Z,9-TDA [J].
JULIA, M ;
STACINO, JP .
TETRAHEDRON, 1986, 42 (09) :2469-2474
[6]  
KANG SK, 1990, SYNLETT, P591
[7]  
MAKAIYAMA T, 1990, TETRAHEDRON, V46, P265
[8]  
SUEMUNE H, 1988, CHEM PHARM BULL, V36, P3632
[9]   A STEREOCONTROLLED CYCLOPENTENONE SYNTHESIS VIA CYCLO-ADDITION [J].
TROST, BM ;
SEOANE, P ;
MIGNANI, S ;
ACEMOGLU, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (19) :7487-7500
[10]   A CONVENIENT SYNTHESIS OF GAMMA-HYDROXY ALPHA,BETA-UNSATURATED SULFONES [J].
TROST, BM ;
GRESE, TA .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) :3189-3192
1