A sequential o-nitrosoaldol and Grignard addition process: an enantio- and diastereoselective entry to chiral 1,2-diols.
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).
Jiao
Peng
P
Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637, USA.
Kawasaki
Masanori
M
Yamamoto
Hisashi
H