We thank J. R. Frowijn for his experimental work.
Synthesis of D-(+)-Biotin through Selective Ring Closure of N-Acyliminium Silyl Enol Ethers†
Article first published online: 22 DEC 2003
Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany
Angewandte Chemie International Edition in English
Volume 34, Issue 21, pages 2391–2393, November 17, 1995
How to Cite
Moolenaar, M. J., Speckamp, W. N., Hiemstra, H., Poetsch, E. and Casutt, M. (1995), Synthesis of D-(+)-Biotin through Selective Ring Closure of N-Acyliminium Silyl Enol Ethers. Angew. Chem. Int. Ed. Engl., 34: 2391–2393. doi: 10.1002/anie.199523911
- Issue published online: 22 DEC 2003
- Article first published online: 22 DEC 2003
- Manuscript Received: 9 JUN 1995
- acyliminium ions;
- silyl enol ethers;
- total syntheses
Irrespective of the geometry of the double bond the configuration of the newly formed chiral center is established by the existing adjacent stereogenic center in the Lewis acid catalyzed cyclization of the N-acyliminium silyl enol ether intermediate 1. This step is the key transformation in a new, concise total synthesis of D-( + )-biotin. R protecting group.