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Rhodium‐Catalyzed Desymmetrization by Hydroformylation of Cyclopentenes: Synthesis of Chiral Carbocyclic Nucleosides
Author(s) -
You Cai,
Wei Biao,
Li Xiuxiu,
Yang Yusheng,
Liu Yue,
Lv Hui,
Zhang Xumu
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201601478
Subject(s) - desymmetrization , hydroformylation , cyclopentane , chemistry , catalysis , rhodium , hydroxymethyl , stereochemistry , organic chemistry , combinatorial chemistry , enantioselective synthesis
Excellent enantioselectivities (up to 97 % ee ) and diastereoselectivities (up to >99:1 d.r.) have been achieved in the desymmetrization of cyclopentenes by catalytic hydroformylation. This novel methodology provides an efficient and concise synthetic route to chiral cyclopentane carboxaldehydes. The key intermediate, (1 S ,3 S )‐(3‐hydroxymethyl)cyclopentanol, for the synthesis of carbocyclic‐ddA was obtained in three steps.
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