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Full Paper
Dinuclear Zinc-Catalyzed Asymmetric Desymmetrization of Acyclic 2-Substituted-1,3-Propanediols: A Powerful Entry into Chiral Building Blocks
Article first published online: 24 JUL 2008
DOI: 10.1002/chem.200800623
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Trost, Barry M., Malhotra, S., Mino, T. and Rajapaksa, Naomi S. (2008), Dinuclear Zinc-Catalyzed Asymmetric Desymmetrization of Acyclic 2-Substituted-1,3-Propanediols: A Powerful Entry into Chiral Building Blocks. Chem. Eur. J., 14: 7648–7657. doi: 10.1002/chem.200800623
Publication History
- Issue published online: 25 AUG 2008
- Article first published online: 24 JUL 2008
- Manuscript Received: 3 APR 2008
Funded by
- National Science Foundation
- National Institutes of Health. Grant Number: GM-33049
Keywords:
- asymmetric catalysis;
- chiral building blocks;
- desymmetrization;
- enantioselectivity;
- propanediol
Abstract
The asymmetric acylation of meso-2-substituted-1,3-propanediols by using an amphoteric chiral dinuclear zinc catalyst is described. It is has been demonstrated that both 2-alkyl- and 2-aryl-1,3-propanediols can be desymmetrized in high yields and enantioselectivities by using the same family of ligands. Given that both antipodes of the chiral catalyst are available, both enantiomers of the desymmetrized product can be obtained from the same starting material. The synthetic utility of the desymmetrized products has been demonstrated by the synthesis of several chiral building blocks with high enantiomeric purities.