☆ 4.4 Article

A novel tandem ene/Prins cyclization for the synthesis of octahydropyrano[2,3-c]pyrrole derivatives

TETRAHEDRON LETTERS (2012)

Journal

TETRAHEDRON LETTERS

Volume 53, Issue 14, Pages 1790-1793

Publisher

PERGAMON-ELSEVIER SCIENCE LTD

DOI: 10.1016/j.tetlet.2012.01.117

Keywords

Tandem reactions; ene/Prins cyclization; cis-fused heterocycles; Scandium(III) triflate

Categories

Chemistry, Organic

Funding

King Saud University for Global Research Network for Organic Synthesis (GRNOS)
CSIR, New Delhi

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Abstract

A tandem ene/Prins cyclization of olefin tethered aldehyde with an aldehyde has been accomplished using 5 mol % scandium triflate at ambient temperature to afford a novel series of cis-fused octahydropyrano[2,3-c]pyrrole derivatives in good yields with high selectivity. This is the first report on a tandem cyclization of 4-methyl-N-(3-methylbut-2-enyl)-N-(2-oxoethyl)benzenesulfonamide with aldehydes. (C) 2012 Elsevier Ltd. All rights reserved.

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