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Preparation and nucleophilic substitution of (e)-1-bromo-2-phenylsulfonyl-2-alkenes and 3-acetoxy-2-phenylsulfonyl-1-alkenes

✍ Scribed by P. Auvray; P. Knochel; J.F. Normant

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 650 KB
Volume: 44
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)89799-4

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✦ Synopsis

5~ -Vinyl phenyl sulfone reacts with aldehydes to yield sulfonylated secondary allylic alcohols which are converted to either primary allylic bromides, or secondary allylic acetates. Both react highly regioselectively with lithium cyanocuprates, or enolates.

We have recently reported the mUlticoupling ability of 3-bromo 2-ter-butylsulfonyl propene, 2 2' 2 2 2' 30 4

which may be used either as an a fa synthon, or as a d fa synthon (in the presence of Zinq (Scheme 1) Scheme 1

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