This work was supported by the Deutsche Forschungsgemeinschaft (Project He 880/7) and by Thomae, Biberach (Germany). A. S. was awarded a grant by the Deutsche Akademische Austauschdienst. We thank Frl. Dipl.-Chem. G. Heiligenmann for the examples No. 10, 11, 17, 18 (Table 1). Part of this work was presented in lectures at the Universities of Göttingen (June 2, 1980), Freiburg (June 9. 1980), and München (July 25, 1980).
Functional Groups at Concave Sites: Asymmetric Alkylation of Esters with Very High Stereoselectivity and Reversal of Configuration by Change of Solvent†
Article first published online: 22 DEC 2003
Copyright © 1981 by Verlag Chemie, GmbH, Germany
Angewandte Chemie International Edition in English
Volume 20, Issue 2, pages 207–208, February 1981
How to Cite
Schmierer, R., Grotemeier, G., Helmchen, G. and Selim, A. (1981), Functional Groups at Concave Sites: Asymmetric Alkylation of Esters with Very High Stereoselectivity and Reversal of Configuration by Change of Solvent. Angew. Chem. Int. Ed. Engl., 20: 207–208. doi: 10.1002/anie.198102071
- Issue published online: 22 DEC 2003
- Article first published online: 22 DEC 2003
- Manuscript Received: 24 SEP 1980
An excellent asymmetric induction (enantiomeric excess >90%) is achieved in the α-alkylation of esters of carboxylic acids and the alcohols (1) or (2) (see previous contribution). A drastic solvent effect (THF or THF-HMPT 4:1) enables each of both enantiomers of a compound to be synthesized in high optical purity.