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Tetrazolic Acid Functionalized Dihydroindol: Rational Design of a Highly Selective Cyclopropanation Organocatalyst

Antti Hartikka and Per I. Arvidsson*

*Department of Biochemistry and Organic Chemistry, Uppsala University, Box 576, SE-75123 Uppsala, Sweden, Email: per.arvidssonbiorg.uu.se

A. Hartikka, P. I. Arvidsson, J. Org. Chem., 2007, 72, 5874-5877.

DOI: 10.1021/jo070519e (free Supporting Information)


Abstract

(S)-(-)-indoline-2-yl-1H-tetrazole readily facilitates the enantioselective organocatalytic cyclopropanation of α,β-unsaturated aldehydes with sulfur ylides, providing cyclized product in excellent diastereoselectivities and enantioselectivities.

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Key Words

Corey-Chaykovsky Reaction, Cyclopropanes, Organocatalysis


ID: J42-Y2007-2380