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Selective epoxidation of 2-(phenylsulfonyl) 1,3-dienes. One-pot procedure for regioselective preparations of 2-(phenylsulfonyl) 1,3-diene monoepoxides from 1,3-dienes

✍ Scribed by Baeckvall, Jan E.; Ericsson, Anna M.; Juntunen, Seppo K.; Najera, Carmen; Yus, Miguel

Book ID
127051832
Publisher
American Chemical Society
Year
1993
Tongue
English
Weight
585 KB
Volume
58
Category
Article
ISSN
0022-3263

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A one-pot procedure for the transformation of a 1,3-diene into the corresponding 2-(phenylsulfonyl)-1,3-diene was developed. The reaction involves a 1,2-selenosulfonation-oxidation sequence. 2-( Phenylsulfonyl)-1,3-dienes have recently been shown to be versatile synthons in organic transformations.

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Reaction of 1-indolylmagnesium iodidelo with the appropriate sulfonyldiene in benzene-ether (1: 1) at 0 "C resulted in a cycloaddition and after workup the teaahydrocarbazole product was isolated. Results from the reaction of a few 2-phenylsulfonyl 1,3-dienes are given in Table 1. In all cases only