Nucleophilic substitutions of 1-alkenylcyclopropyl esters and 1-alkynylcyclopropyl chlorides catalyzed by palladium (0)

A Stolle, J Ollivier, PP Piras, J Salaun…

Index: Stolle, Andreas; Ollivier, Jean; Piras, Pier Paolo; Salauen, Jacques; De Meijere, Armin Journal of the American Chemical Society, 1992 , vol. 114, # 11 p. 4051 - 4067

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Citation Number: 101

Abstract

Abstract: The 1-ethenylcyclopropylsulfonates 2e, f and 2-cyclopropylideneethyl esters lob $, readily available from cyclopropanone hemiacetal 1, undergo regioselective Pd (0) catalyzed nucleophilic substitution via the unsymmetric 1, l-dimethylene-a-allyl complex 23. With stabilized anions (enolates of malonic ester,@-dicarbonyl compounds,@-sulfonyl ester, and Schiff bases as well as acetate anion, sulfonamide anion, etc.) the nucleophilic ...