Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 9, Pages 2828-2831Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja1098353
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- NUS
- [R-143-000-342-112]
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A new chiral entity, pentanidium, has been shown to be an excellent chiral phase-transfer catalyst. The enantioselective Michael addition reactions of tert-butyl glycinate-benzophenone Schiff base with various alpha, beta-unsaturated acceptors provide adducts with high enantioselectivities. A successful gram-scale experiment at a low catalyst loading of 0.05 mol % indicates the potential for practical applications of this methodology. Phosphoglycine ester analogues can also be utilized as the Michael donor, affording enantioenriched alpha-aminophosphonic acid derivatives and phosphonic analogues of (S)-proline.
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