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A Sequential O‐Nitrosoaldol and Grignard Addition Process: An Enantio‐ and Diastereoselective Entry to Chiral 1,2‐Diols
Author(s) -
Jiao Peng,
Kawasaki Masanori,
Yamamoto Hisashi
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200900682
Subject(s) - cyclohexanone , tetrahydrofuran , chemistry , grignard reagent , sulfoxide , grignard reaction , medicinal chemistry , derivative (finance) , reagent , catalysis , organic chemistry , solvent , financial economics , economics
Chiral 1,2‐diols have been prepared from α ‐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).