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

Jiao Peng | Zendy; Kawasaki Masanori | Zendy; Yamamoto Hisashi | Zendy

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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).

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