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A Simple, Efficient, and Highly Enantioselective Synthesis of MS-153 Employing a Chiral Silane Lewis Acid-Promoted Acylhydrazone-Enol Ether [3+2] Cycloaddition
Article first published online: 27 NOV 2006
DOI: 10.1002/adsc.200600357
Copyright © 2006 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Advanced Synthesis & Catalysis
Special Issue: Catalytic Cycloaddition Reactions
Volume 348, Issue 16-17, pages 2431–2436, November 2006
Additional Information
How to Cite
Tran, K. and Leighton, James L. (2006), A Simple, Efficient, and Highly Enantioselective Synthesis of MS-153 Employing a Chiral Silane Lewis Acid-Promoted Acylhydrazone-Enol Ether [3+2] Cycloaddition. Adv. Synth. Catal., 348: 2431–2436. doi: 10.1002/adsc.200600357
Publication History
- Issue published online: 27 NOV 2006
- Article first published online: 27 NOV 2006
- Manuscript Accepted: 15 SEP 2006
- Manuscript Received: 15 JUL 2006
- Abstract
- References
- Cited By
Keywords:
- acylhydrazones;
- cycloaddition;
- enantioselectivity;
- Lewis acids;
- MS-153;
- silicon
Abstract
Our previously reported chiral silane-promoted enol ether-acylhydrazone [3+2] cycloaddition reaction has been applied to a brief and efficient synthesis of the neuroprotective agent MS-153. Unsatisfactory and variable levels of efficiency and enantioselectivity with the requisite acetaldehyde-derived acylhydrazone occasioned a modification to the chiral silane Lewis acid, which led to the key cycloaddition step proceeding with excellent efficiency (85 % yield) and enantioselectivity (≥98 % ee).