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A Sequential O‐Nitrosoaldol and Grignard Addition Process: An Enantio‐ and Diastereoselective Entry to Chiral 1,2‐Diols
Authors:Peng Jiao Dr  Masanori Kawasaki Dr  Hisashi Yamamoto Prof?Dr
Institution:Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637 (USA), Fax: (+1)?773‐702‐0805
Abstract: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 CeCl3?2 LiCl is essential for the high overall yields and good selectivities (see scheme; DMSO=dimethyl sulfoxide, THF=tetrahydrofuran, Tol=tolyl).
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Keywords:asymmetric synthesis  diastereoselective synthesis  1  2‐diols  synthetic methods
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