Journal of Organic Chemistry 2001-09-07

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

P Langer, E Holtz, I Karimé, N N Saleh

Index: J. Org. Chem. 66(18) , 6057-63, (2001)

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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.