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A Facile and Rapid Route to Highly Enantiopure 1,2‐Diols by Novel Catalytic Asymmetric α‐Aminoxylation of Aldehydes
Author(s) -
Zhong Guofu
Publication year - 2003
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.200352097
Subject(s) - enantiopure drug , nitrosobenzene , catalysis , diol , chemistry , sequence (biology) , combinatorial chemistry , enantioselective synthesis , computer science , organic chemistry , biochemistry
R ‐ or S ‐configured 1,2‐diol precursors are formed in good yields (54–86 %) and with excellent enantioselectivities (94 to 99 % ee ) by using a simple one‐pot sequence—catalytic α‐aminoxylation of aldehydes followed by in situ reduction with NaBH 4 —with L ‐ or D ‐proline as the catalyst and nitrosobenzene as the oxygen source (see scheme).
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