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Facile cycloaddition of 2-phenylsulfonyl 1,3-dienes to indoles

✍ Scribed by Jan-E. Bäckvall; Niklas A. Plobeck; Seppo K. Juntunen

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
236 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 one regioisomer was formed

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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.