Tetrahedron letters

Regioselective ring cleavage of chiral β-trichloromethyl-β-propiolactone with organoaluminum compounds for the synthesis of optically active intermediates

T Fujisawa, T Ito, S Nishiura, M Shimizu

Index: Fujisawa, Tamotsu; Ito, Takatoshi; Nishiura, Shin; Shimizu, Makoto Tetrahedron Letters, 1998 , vol. 39, # 52 p. 9735 - 9738

Full Text: HTML

Citation Number: 16

Abstract

A novel alkylating ring cleavage reaction of enantiomerically pure β-trichloromethyl-β- propiolactone as a chiral building block with organoaluminum compounds provided ring- opened products with a chiral trichloromethyl carbinol moiety. A product was demonstrated to be used as an effective chiral synthon for the synthesis of chiral bioactive derivatives such as ipsdienol and sodium cilastatin.