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Proline‐Tetrazole‐Catalyzed Enantioselective N ‐Nitroso Aldol Reaction of Aldehydes with In Situ Generated Nitrosocarbonyl Compounds
Author(s) -
Maji Biplab,
Yamamoto Hisashi
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201311069
Subject(s) - aldol reaction , tetrazole , enantioselective synthesis , chemistry , catechol , catalysis , nitroso , proline , organic chemistry , in situ , brønsted–lowry acid–base theory , combinatorial chemistry , amino acid , biochemistry
A highly enantioselective method (up to 98 % ee ) for the preparation of β‐amino alcohols was achieved by using the readily available proline‐tetrazole as the catalyst for the N ‐nitroso aldol reaction of aldehydes with in situ generated nitrosocarbonyl compounds. The key to success of this reaction is the use of MnO 2 as an oxidant and catechol as a Brønsted acid additive.
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