Selective oxidation of phosphorus ylides by dimethyldioxirane. Application to the formation of vicinal tricarbonyls

HH Wasserman, CM Baldino…

Index: Wasserman, Harry H.; Baldino, Carmen M.; Coats, Steven J. Journal of Organic Chemistry, 1995 , vol. 60, # 25 p. 8231 - 8235

Full Text: HTML

Citation Number: 51

Abstract

Dimethyldioxirane (DMD) has proven to be an effective reagent for the selective conversion of phosphoranylidene intermediates 4 to the corresponding vicinal tricarbonyls 5. Unlike existing oxidation protocols which employ relatively vigorous conditions, this transformation is conducted rapidly at low temperature under neutral conditions, without the necessity of an aqueous workup. Selective oxidation of the phosphorus ylides in the presence of a variety ...