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Iridium‐Catalyzed Dynamic Kinetic Isomerization: Expedient Synthesis of Carbohydrates from Achmatowicz Rearrangement Products
Author(s) -
Wang HaoYuan,
Yang Ka,
Bennett Scott R.,
Guo Shengrong,
Tang Weiping
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201503151
Subject(s) - isomerization , chemistry , catalysis , enantiomer , stereoselectivity , kinetic resolution , iridium , combinatorial chemistry , redox , reaction mechanism , enantioselective synthesis , organic chemistry
A highly stereoselective dynamic kinetic isomerization of Achmatowicz rearrangement products was discovered. This new internal redox isomerization provided ready access to key intermediates for the enantio‐ and diastereoselective synthesis of a series of naturally occurring sugars. The nature of the de novo synthesis also enables the preparation of both enantiomers.