This work was generously supported by the Deutsche Forschungsgemeinschaft (Li 556/2-1, Li 556/3-1) and the Universitätsbund Würzburg. We thank Prof. W. Adam for his continuous encouragement.
Highly Diastereoselective Synthesis and Epoxidation of Chiral 1,2-Dihydronaphthalenes†
Article first published online: 22 DEC 2003
Copyright © 1996 by VCH Verlagsgesellschaft mbH, Germany
Angewandte Chemie International Edition in English
Volume 35, Issue 21, pages 2487–2489, November 18, 1996
How to Cite
Linker, T., Peters, K., Peters, E.-M. and Rebien, F. (1996), Highly Diastereoselective Synthesis and Epoxidation of Chiral 1,2-Dihydronaphthalenes. Angew. Chem. Int. Ed. Engl., 35: 2487–2489. doi: 10.1002/anie.199624871
- Issue published online: 22 DEC 2003
- Article first published online: 22 DEC 2003
- Manuscript Received: 7 JUN 1996
- asymmetric syntheses;
- naphthalene derivatives;
- synthetic methods
Four stereogenic centers are generated with high diastereoselectivity in only a few steps starting from 2-naphthoic acid (1). Meyers oxazoline synthesis, nucleophilic addition of phenyllithium, and epoxidation afford rac-2 in 63% overall yield. The stereochemical course of the reaction is directed by the phenyl group.