- 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...
Expand abstract - Publication status:
- Published
- Publisher copy:
- 10.1021/ja061104y
-
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- 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
- Copyright date:
- 2006
Journal article
Heterogeneously catalyzed asymmetric C=C hydrogenation: origin of enantioselectivity in the proline-directed Pd/isophorone system.
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