This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie.
Article first published online: 22 DEC 2003
Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany
Angewandte Chemie International Edition in English
Volume 34, Issue 16, pages 1731–1733, September 1, 1995
How to Cite
Tietze, L. F. and Schünke, C. (1995), Intramolecular Allylsilane Addition to Chiral Alkylidene-1,3-dicarbonyl Compounds for the Synthesis of Enantiomerically Pure trans-1,2-Disubstituted Cyclopentanes and Cyclohexanes. Angew. Chem. Int. Ed. Engl., 34: 1731–1733. doi: 10.1002/anie.199517311
Dedicated to Professor Herbert W. Roesky on the occasion of his 60th birthday
- Issue published online: 22 DEC 2003
- Article first published online: 22 DEC 2003
- Manuscript Received: 4 MAR 1995
- asymmetric syntheses;
Three new stereogenic centers characterize the 1,2-trans-disubstituted cyclopentanes 2a and cyclohexanes 2b, which can be prepared enantiomerically pure with the Lewis acid SnCl4 in a highly selective SnCl4-induced cyclization of the chiral alkylidene malonic acid derivatives 1a and 1b, respectively. The chiral auxiliary can be removed from 2 with LiAlH4.