Issue 11, 1993

Chiral induction in aryl radical cyclization to the aldimino functional group

Abstract

6-endo Cyclization of aryl radicals to carbon of aldimino double bonds (N-5/C-6) in chiral ortho-substituents afforded 1,2,3,4-tetrahydroisoquinolines in yields to 69%, with 58% d.e. and 97% e.e., while 5-exo Cyclization to carbon in isomeric radicals (C-5/N-6 aldimine), leading to indanamines, was highly regioselective and fast, k5-exo= 3.9 × 108s–1 at 80 °C.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1993, 966-968

Chiral induction in aryl radical cyclization to the aldimino functional group

M. J. Tomaszewski and J. Warkentin, J. Chem. Soc., Chem. Commun., 1993, 966 DOI: 10.1039/C39930000966

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