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Volumn 5, Issue 21, 2007, Pages 3407-3417

Asymmetric organocatalytic reductions mediated by dihydropyridines

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL SYSTEMS; CATALYST ACTIVITY; ENZYME ACTIVITY; HYDRIDES; REDUCTION;

EID: 35348853794     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b711499k     Document Type: Article
Times cited : (174)

References (185)
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    • Karrer and co-workers had earlier shown that 1,4-dihydropyridines could reduce methylene blue, however, proof of direct hydrogen transfer could not be obtained (via deuterium labelling experiments) due to the likelihood of fast exchange of the transferred H/D in the product with the solvent.
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    • For a later study demonstrating the reduction of other keto acids see:
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    • For a recent example of a chiral metal-based catalyst promoting enantioselective reductions of α-keto esters using stoichiometric loadings of a Hanztsch dihydropyridine see:
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    • For a review concerning recent developments in both metal-free and metal-assisted Brønsted acid catalysts see:
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    • For reports concerning the reduction of imines/reductive amination of aldehydes/ketones using achiral thiourea catalysts see:
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    • The authors use optical rotation data to determine levels of enantiomeric excess and cite previous work by Kagan et al., curiously the absolute configuration of 36 is not given by Singh even though it was determined by Kagan. We have assumed that Singh used the same conditions as Kagan in assigning the absolute configuration of 36:
    • S. Singh U. K. Batra Ind. J. Chem. 1989 28B 1
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    • For a short monograph concerning the use of chiral phosphoric acids as catalysts for enantioselective addition reactions to imines see:
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    • John Wiley & Sons, New York, For a review detailing the use of phosphoric acid catalysts in other asymmetric transformations see ref. 6i
    • a of diethyl phosphate is 1.39: L. D. Quin, A Guide to Organophosphorus Chemistry, John Wiley & Sons, New York, 2000, ch. 5
    • (2000) A Guide to Organophosphorus Chemistry
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    • For a previous example where VAPOL-derived phosphoric acids proved superior to BINOL-based materials see:
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    • The authors point out that combining asymmetric processes results in a mathematical requirement for an improvement in enantioselectivity. For example, if two catalytic cycles are combined, both of which give products with 86% ee, the cascade will give a 7: 1 mixture of diastereomers and the major diastereomer will be formed in 99% ee
    • Y. Huang A. M. Walji C. H. Larsen D. W. C. MacMillan J. Am. Chem. Soc. 2006 127 15051
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    • For a similar strategy in a photoinduced dihydropyridine-mediated reduction of chalcone oxides not under the influence of catalysis see:
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    • Procuranti, B.1    Connon, S.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.