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Stereoselective reduction of chiral 2-furoic acid derivatives using group I metals in ammonia

Abstract:

A series of chiral auxiliaries have been attached to 2-furoic acid and 3-methyl-2-furoic acid. The performance of these auxiliaries in the Birch reduction was assessed and it was found that placing a C-3 methyl group on the heterocycle was essential for good stereoselectivity. Using bis(methoxymethyl)pyrrolidine high levels of diastereoselectivity could be obtained with a range of electrophiles. A model is also presented which explains the sense of stereoselectivity displayed by this auxiliar...

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Publication status:
Published

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Publisher copy:
10.1039/b006390h

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Issue:
22
Pages:
3724-3731
Publication date:
2000-01-01
DOI:
EISSN:
1364-5463
ISSN:
1470-4358
URN:
uuid:53f36091-0903-4bfc-847a-45c3f9bb3b00
Source identifiers:
37575
Local pid:
pubs:37575
Language:
English

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