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Palladium-catalyzed oxidative cyclizations: synthesis of dihydropyranones and furanones.

Abstract:

A boron-mediated syn- and anti-stereoselective aldol reaction giving rise to various beta-hydroxyenones was coupled to a Pd((II))-mediated oxidative cyclization to give 2,3,6-trisubstituted syn- and anti-dihydropyranones in good yields. The Pd((II))-mediated oxidative cyclization was expanded to alpha-hydroxyenones leading to furan-3(2H)-one derivatives, which include natural product bullatenone and a known precursor of geiparvarin. The sole product of the oxidative cyclization of alpha,beta-...

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Publication status:
Published

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Publisher copy:
10.1021/jo051274d

Authors


Mills-Webb, R More by this author
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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
The Journal of organic chemistry
Volume:
70
Issue:
21
Pages:
8478-8485
Publication date:
2005-10-05
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
URN:
uuid:7b889fce-90ad-4f23-b227-0c750fcd51f5
Source identifiers:
33255
Local pid:
pubs:33255
Language:
English

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