Alkene synthesis from allylic sulfones: Preparation of isopropenyl and isopropylidene isomers from a common intermediate

被引:19
作者
Phillips, ED [1 ]
Warren, ES [1 ]
Whitham, GH [1 ]
机构
[1] UNIV OXFORD,DYSON PERRINS LAB,OXFORD OX1 3QY,ENGLAND
关键词
D O I
10.1016/S0040-4020(96)00986-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Using alpha-alkylation, 1,3-rearrangement, and regioselective desulfonylation allows the control of the regiochemistry of alkene synthesis from allylic sulfones. Sequences involving allylic 2-hydroxypropyl, 2-trimethylsilylethyl, and benzothiazol-2-yl sulfones are described leading to isopropenyl and isopropylidene isomers of an alkene starting from a common sulfone intermediate. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:307 / 320
页数:14
相关论文
共 56 条
[51]   RADICAL INDUCED CYCLIZATIONS OF SOME CYCLIC UNSATURATED ALLYLIC SULFONES [J].
SMITH, TAK ;
WHITHAM, GH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (02) :313-317
[52]   RADICAL INDUCED 1,3-REARRANGEMENT-CYCLIZATIONS OF SOME UNSATURATED ALLYLIC SULFONES [J].
SMITH, TAK ;
WHITHAM, GH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (02) :319-325
[53]   MIGRATION APTITUDE OF BENZYL VS METHYL IN CARBONIUM ION REACTIONS OF 2,2-DIMETHYL-3-PHENYL-1-PROPYL SYSTEM [J].
WARRICK, P ;
SAUNDERS, WH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (21) :4095-&
[54]   THE PREPARATION, STRUCTURE AND PROPERTIES OF THE DIMER OF METHALLYL CHLORIDE [J].
WILZBACH, KE ;
MAYO, FR ;
VANMETER, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (12) :4069-4072
[55]  
WISLICENUS H, 1895, CHEM BER, V28, P1323
[56]   ASYMMETRIC [3 + 2] CYCLO-ADDITION OF 2-(SULFONYLMETHYL)-2-PROPENYL CARBONATE CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-PALLADIUM COMPLEXES [J].
YAMAMOTO, A ;
ITO, Y ;
HAYASHI, T .
TETRAHEDRON LETTERS, 1989, 30 (03) :375-378