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Chemoselective, Regioselective, and E/Z-Diastereoselective Synthesis of 2-Alkylidenetetrahydrofurans by Sequential Reactions of Ambident Dianions and Monoanions

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journal contribution
posted on 12.12.2003, 00:00 by Peter Langer, Esen Bellur
A number of novel β-ketoesters were prepared by regioselective alkylation reactions of simple β-ketoester dianions. The cyclization of the dianions of these 1,3-dicarbonyl derivatives with 1-bromo-2-chloroethane afforded a variety of 2-alkylidenetetrahydrofurans with very good regioselectivity and E/Z-diastereoselectivity. These products were deprotonated to give novel ambident carbanions. The alkylation of these carbanions with alkyl halides proceeded with very good regioselectivity and E/Z-diastereoselectivity and allowed a convenient synthesis of a great variety of new 2-alkylidenetetrahydrofurans.