Tetrahedron letters

A useful and convenient synthetic protocol for interconversion of carbonyl compounds to the corresponding 1, 3-oxathiolanes and vice versa employing organic …

E Mondal, PR Sahu, G Bose, AT Khan

Index: Mondal, Ejabul; Sahu, Priti Rani; Bose, Gopal; Khan, Abu T. Tetrahedron Letters, 2002 , vol. 43, # 15 p. 2843 - 2846

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Citation Number: 73

Abstract

A wide variety of carbonyl compounds 1 can be easily protected selectively as the corresponding 1, 3-oxathiolanes 2 in good yields using a catalytic amount (0.01–0.1 equiv.) of n-tetrabutylammonium tribromide in dry CH2Cl2 at 0–5° C. On the other hand, various 1, 3- oxathiolanes 2 can be deprotected chemoselectively to the parent carbonyl compounds 1 employing 0.5 equivalents of organic ammonium tribromides under identical conditions in ...