A D,L-proline catalyzed diastereoselective trimolecular condensation: an approach to the one-pot synthesis of perhydrofuro[3,2-b]pyran-5-ones

Sabitha, Gowravaram ; Raj Kumar, M. ; Shashi Kumar Reddy, M. ; Yadav, J. S. ; Rama Krishna, K. V. S. ; Kunwar, A. C. (2005) A D,L-proline catalyzed diastereoselective trimolecular condensation: an approach to the one-pot synthesis of perhydrofuro[3,2-b]pyran-5-ones Tetrahedron Letters, 46 (10). pp. 1659-1661. ISSN 0040-4039

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.tetlet.2005.01.071

Abstract

D,L-Proline was found to catalyze efficiently the one-pot trimolecular condensation of indoles, a sugar hydroxyaldehyde, and Meldrum's acid followed by intramolecular cyclization with evolution of carbon dioxide and elimination of acetone to afford 7-(1H-3-indolyl)-2,3-dimethoxyperhydrofuro[3,2-b]pyran-5-ones. The reaction proceeded cleanly at ambient temperature to afford the products in good yields with high diastereoselectivity.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:D,L-proline; Furo-pyranone; Indole; Trimolecular Condensation
ID Code:58826
Deposited On:02 Sep 2011 03:21
Last Modified:02 Sep 2011 03:21

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