A Sequential O‐Nitrosoaldol and Grignard Addition Process: An Enantio‐ and Diastereoselective Entry to Chiral 1,2‐Diols

Abstract

Chiral 1,2-diols have been prepared from alpha-aminoxylated aldehydes or cyclohexanone and Grignard reagents with L-proline or its tetrazole derivative as the catalyst. The presence of the ate complex of CeCl(3)2 LiCl is essential for the high overall yields and good selectivities (see scheme; DMSO = dimethyl sulfoxide, THF = tetrahydrofuran, Tol = tolyl).