SYNTHESIS, DEPROTONATION, AND ALKYLATION OF S-ALLYL SULFOXIMINES

被引:29
作者
HARMATA, M
CLAASSEN, RJ
机构
[1] Department of Chemistry, University of Missouri-Columbia, Columbia
关键词
D O I
10.1016/0040-4039(91)80202-H
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Phenyl-S-(4-methylphenyl)-sulfoximidoyl chloride 1 reacts with allyltrimethylsilane in the presence of aluminum chloride to give benzothiazine 4 in fair yield along with a small amount of S-allyl sulfoximine 3a. On the other hand, 1 reacts with allyltributyltin to give the S-allyl sulfoximine 3a almost exclusively. This latter reaction appears to be general. The sulfoximine 3a is thermally stable and can be deprotonated smoothly with n-BuLi. The anion reacts regioselectively but not stereoselectively with simple alkylating agents. Reactions of the anion with selected aldehydes and enones proceeds with some regiocontrol and, with some exceptions, little stereocontrol.
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页码:6497 / 6500
页数:4
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