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Highly Diastereoselective Synthesis of the 1,1'-Binaphthol Unit on a Bile Acid Template

Bandyopadhyaya, Achintya K and Sangeetha, NM and Maitra, Uday (2000) Highly Diastereoselective Synthesis of the 1,1'-Binaphthol Unit on a Bile Acid Template. In: Journal of Oraganci Chemistry, 65 (24). pp. 8239-8244.

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo000703z

Abstract

The use of 7-deoxycholic acid as a chiral template in the asymmetric syntheses of 1,1'-binaphthyl-2,2'-diol derivatives is reported. Intramolecular coupling of compounds 7 and 11 have been carried out with Mn(acac)(3) in CH3CN to afford coupled binaphthol products 8 and 12 with 65% and >99% diastereoselectivity, respectively. In both cases the predominant formation of the (S) isomers were predicted by computer modeling studies. This was confirmed in the case of compound 12.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to American Chemical Society.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 12 Aug 2009 08:05
Last Modified: 19 Sep 2010 04:58
URI: http://eprints.iisc.ernet.in/id/eprint/17770

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