Tetrahedron Letters

Cyclization of N, N-diethylgeranylamine N-oxide in one-pot operation: preparation of cyclic terpenoid-aroma chemicals

K Takabe, T Yamada, T Miyamoto, N Mase

Index: Takabe, Kunihiko; Yamada, Takashi; Miyamoto, Takenori; Mase, Nobuyuki Tetrahedron Letters, 2008 , vol. 49, # 41 p. 6016 - 6018

Full Text: HTML

Citation Number: 3

Abstract

Acid promoted cyclization of the geranylamine N-oxide (E)-4 followed by base-catalyzed intramolecular aldol condensation afforded 1-acetyl-4, 4-dimethyl-1-cyclohexene (7) in one- pot operation. Reduction of 7, which possess strong fruity odor, followed by lipase-catalyzed kinetic resolution furnished the acetate (R)-26 (> 49.9% yield,> 99% ee) and the recovered alcohol (S)-25 (> 49.9% yield,> 99% ee, herbal odor).