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A catalytic asymmetric bioorganic route to enantioenriched tetrahydro- and dihydropyranones.

Abstract:

A conceptually novel approach to hetero Diels-Alder adducts of carbonyl compounds is described using as the key steps an antibody-mediated kinetic resolution of hydroxyenones followed by a ring-closure process. Various beta-hydroxyenones proved to be very good substrates for antibodies 84G3- and 93F3-catalyzed retro-aldol reactions, allowing the preparation of highly enantiomerically enriched (up to 99% ee) precursors of pyranones. An attractive feature of this methodology is the possibility ...

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Publication status:
Published

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Publisher copy:
10.1021/ja043925d

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Journal:
Journal of the American Chemical Society
Volume:
127
Issue:
5
Pages:
1481-1486
Publication date:
2005-02-05
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
URN:
uuid:ba1aa452-44e8-44ae-a1fe-455e3d307b29
Source identifiers:
32975
Local pid:
pubs:32975
Language:
English

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