Diastereoselective tandem addition-cyclization reactions of unsaturated tertiary amines initiated by photochemical electron transfer (PET)

S Bertrand, N Hoffmann, S Humbel…

Index: Bertrand; Hoffmann; Humbel; Pete Journal of Organic Chemistry, 2000 , vol. 65, # 25 p. 8690 - 8703

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Citation Number: 77

Abstract

Polycyclic molecules and tetrahydroquinoleines were obtained in a tandem reaction involving the diastereoselective addition of α-aminoalkyl radicals to (5 R)-5-menthyloxy-2 [5 H]-furanone 1. The facial diastereoselectivity on 1 is≥ 90%. The α-aminoalkyl radicals were produced from tertiary amines by photochemical-induced electron transfer. When N, N- dialkylanilines 19 were used as starting tertiary amines, a rearomatization step was ...