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Synthesis of enantiopure dihydropyranones: aldol-based ring expansion of dihydrofurans.

Abstract:
[reaction: see text] The stereoselective Birch reduction of 3-methyl-2-furoic acids using a readily available chiral auxilairy is described; by coupling this process to an oxidative cleavage/aldol ring closure sequence we were able to produce highly functionalized and enantiopure dihydropyranones in high yield. This sequence has ample flexibility built into it, either by the use of different electrophiles during reductive alkylation or by subsequent derivatization of the dihydropyranone after ring expansion.
Publication status:
Published

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Publisher copy:
10.1021/ol0263595

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
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Journal:
Organic letters
Volume:
4
Issue:
18
Pages:
3059-3062
Publication date:
2002-09-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:4b4a86e7-f8f2-487f-bd14-027f32a8b68a
Source identifiers:
32186
Local pid:
pubs:32186

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