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2-Pyridylsulfinamides as effective catalysts in the asymmetric alkylation of aldehydes with diethylzinc

Prasad, Kavirayani R and Revu, Omkar (2013) 2-Pyridylsulfinamides as effective catalysts in the asymmetric alkylation of aldehydes with diethylzinc. In: Tetrahedron, 69 (39). pp. 8422-8428.

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Official URL: http://dx.doi.org/10.1016/j.tet.2013.07.061

Abstract

Chiral 2-pyridylsulfinamides were shown to be effective catalysts in the alkylation of aryl and alkyl aldehydes with diethylzinc providing the corresponding alcohols in excellent enantioselectivity. Sulfinamide catalysts possessing solitary chirality at the sulfur center produced the product phenethyl alcohol in good enantioselectivity. Diastereomeric sulfinamides possessing chirality at the carbon-bearing nitrogen and at the sulfur of the sulfinamide increased the enantioselectivity of the product alcohols up to >99%. However, there is no effect of the match-mismatch pair of sulfinamide diastereomers on the outcome of the chiral induction of the product phenethyl alcohols. It was conclusively proved that chirality at the sulfur center is mandatory for obtaining good enantioselectivity in the reaction.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Elsevier Science.
Keywords: Chiral Sulfinamides; Chiral Pyridyl Ligands; Asymmetric Catalysis; Asymmetric Alkylation
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Francis Jayakanth
Date Deposited: 25 Oct 2013 06:31
Last Modified: 25 Oct 2013 06:31
URI: http://eprints.iisc.ac.in/id/eprint/47473

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