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Heterogeneously catalyzed asymmetric C=C hydrogenation: origin of enantioselectivity in the proline-directed Pd/isophorone system.

Abstract:

We have studied the proline-directed, Pd-catalyzed enantioselective hydrogenation of isophorone in the liquid state using a variety of methods. Our results unambiguously reveal the true reaction pathway and demonstrate that all earlier mechanistic hypotheses are wrong: although a proline/isophorone condensation product is formed, it is merely a spectator and not a key reaction intermediate in subsequent heterogeneous hydrogenation. Enantioselectivity is the result of kinetic resolution-a proc...

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Publication status:
Published

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Publisher copy:
10.1021/ja061104y

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
Journal of the American Chemical Society
Volume:
128
Issue:
22
Pages:
7329-7334
Publication date:
2006-06-05
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
URN:
uuid:17fbfca8-37dc-46c6-967b-465494eee716
Source identifiers:
54861
Local pid:
pubs:54861
Language:
English

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