Insight into acid-mediated asymmetric spirocyclization in the presence of a chiral diol

Authors
Kiguchi, T Tsurusaki, Y Yamada, S Aso, M Tanaka, M Sakai, K Suemune, H
Citation
T. Kiguchi et al., Insight into acid-mediated asymmetric spirocyclization in the presence of a chiral diol, CHEM PHARM, 48(10), 2000, pp. 1536-1540
Citations number
9
Categorie Soggetti
Chemistry & Analysis
Journal title
CHEMICAL & PHARMACEUTICAL BULLETIN
ISSN journal
00092363 → ACNP
Volume
48
Issue
10
Year of publication
2000
Pages
1536 - 1540
Database
ISI
SICI code
0009-2363(200010)48:10<1536:IIAASI>2.0.ZU;2-O
Abstract
Asymmetric spirocyclization based on intramolecular conjugate addition usin g a combination of a Lewis acid and an optically active cyclohexane-1,2-dio l has been studied in connection with 1) the effect of substituents on the cylclohexane-1,2-diol and 2) the effect of substituents on the substrate. T his reaction was found to be both thermodynamically and kinetically control led under restricted conditions.