Regio- and diastereoselective alkylation of (1R,5S)-4-ethyl-6,6-dimethyl-3-(phenylsulfonyl)bicyclo[3.1.1]hept-3-en-2-one

Publication Type: Journal contribution
Authors: Kato, M.; Watanabe, M.; Awen, B. Z.; Vogler, B.
Year of publication: 1991
Published in: Tetrahedron Lett.
Band/Volume: 32/50
Page (from - to): 7439-42

Abstract

Alkylation of (1R,5S)-4-ethyl-6,6-dimethyl-3- (phenylsulfonyl)bicyclo[3.1.1]hept-3-en-2-one (I) with allyl bromide proceeded at the .gamma. position to the conjugated enone system in regio- and diastereoselective fashion, providing (1R,5S)-4-((1R)-1-methyl-3-butenyl)-6,6-dimethyl-3-(phenylsulfonyl)bicyclo[3.1.1]hept-3-en-2-one (II) in good yield. An analogous trend was obsd. in alkylation of I with otherrepresentative alkyl halides.

Involved institutions

Institute of Chemistry
Bioorganic Chemistry