Enantioselective desymmetrization of phospholene meso-epoxide by nucleophilic opening of the epoxide

摘要

A convenient synthesis of enantioenriched P-stereogenic trans-3-hydroxy-4-azido- and trans-3-hydroxy-4-cyanophospholane oxides has been achieved by ring opening of 3,4-epoxy-1-phenylphospholane-1-oxide using trimethylsilyl azide and trimethylsilyl cyanide in the presence of salen-Al complex. The enantioselectivity of the studied asymmetric ring-opening reactions reached 72% in the best case. (C) 2003 Elsevier Ltd. All rights reserved. [References: 27]