Insight into Acid-Mediated Asymmetric Spirocyclization in the Presence of a Chiral Diol

Toshihiro KIGUCHI; Yuko TSURUSAKI; Satoshi YAMADA; Mariko ASO; Masakazu TANAKA; Kiyoshi SAKAI; Hiroshi SUEMUNE

doi:10.1248/cpb.48.1536

Toshihiro KIGUCHI, Yuko TSURUSAKI, Satoshi YAMADA, Mariko ASO, Masakazu TANAKA, Kiyoshi SAKAI, Hiroshi SUEMUNE

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Keywords: asymmetric spirocyclization, Lewis acid, 1, 2-diol, kinetic control, thermodynamic control

JOURNAL FREE ACCESS

2000 Volume 48 Issue 10 Pages 1536-1540

DOI https://doi.org/10.1248/cpb.48.1536

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Abstract

Asymmetric spirocyclization based on intramolecular conjugate addition using a combination of a Lewis acid and an optically active cyclohexane-1, 2-diol has been studied in connection with 1) the effect of substituents on the cyclohexane-1, 2-diol and 2) the effect of substituents on the substrate. This reaction was found to be both thermodynamically and kinetically controlled under restricted conditions.

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