Diastereoselective Access to 3??Nitro??4??vinylidenetetrahydrofurans and 3??Nitro??4??vinylidenetetrahydropyrans and Their Conversion into 3, 6??Dihydro??1, 2??oxazines …

E Dumez, R Faure, JP Dulcère

Index: Dumez, Estelle; Faure, Robert; Dulcere, Jean-Pierre European Journal of Organic Chemistry, 2001 , # 13 p. 2577 - 2588

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Citation Number: 26

Abstract

Abstract A new approach to the synthesis of unsaturated nitro-allenyl-tetrahydrofurans 3 and- tetrahydropyrans 5 has been developed, involving oxa-Michael addition/SN 2′ substitution of propargyl and homopropargyl alcohol derivatives 2a and 4h on nitroalkenes 1a− g. Complete allylic 1, 3-strain control during the cyclization accounts for the observed diastereoselectivity. Reduction of nitro compounds 3 and 5 with SmI 2 provided new α− ...