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The Journal of organic chemistry

Regio- and diastereoselective synthesis of 2-alkylidenetetrahydrofurans by domino SN/SN' and SN/SN reactions of 1,3-dicarbonyl dianions.


PMID 11529731

Abstract

The domino C,O-cyclodialkylation reaction of dilithiated 1,3-dicarbonyl compounds with 1,4-dibromo-2-butene resulted in regio- and diastereoselective formation of 2-alkylidene-5-vinyltetrahydrofurans. The cyclization of 1,3-dicarbonyl dianions with 1-bromo-2-chloroethane regio- and diastereoselectively afforded 2-alkylidenetetrahydrofurans under thermodynamic reaction control.

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232750
1-Bromo-2-chloroethane, 98%
C2H4BrCl