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Synlett 1996; 1996(7): 640-642
DOI: 10.1055/s-1996-5543
DOI: 10.1055/s-1996-5543
letter
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5- and 6-Exo Radical Cyclizations of γ-Oxygenated-α,β-Unsaturated Sulfones
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Publication History
Publication Date:
31 December 2000 (online)
Bromo γ-oxygenated-α,β-unsaturated sulfones 1 and 2 underwent efficient 5- and 6-exo radical cyclizations, respectively, by reaction with Bu3SnH/AIBN without using slow addition techniques. The presence of a double bond joined to the oxygen, such as the OCH=CH-CO2Me moiety of substrates 5 and 6, allowed the preparation of [3.3.0] and [4.3.0] bicyclic compounds according to a tandem sequence based on two consecutive radical cyclizations.
Radical - cyclization - α,β-unsaturated sulfones - tandem process - stereoselectivity