Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/25242
Title: Zinc bromide as catalyst for the stereoselective construction of quaternary carbon: Improved synthesis of diastereomerically enriched spirocyclic diols
Authors: Tu, YQ
Fan, CA
Ren, SK
Chan, ASC
Issue Date: 2000
Publisher: Royal Society of Chemistry
Source: Journal of the Chemical Society. Perkin transactions 1, 2000, no. 22, p. 3791-3794 How to cite?
Journal: Journal of the Chemical Society. Perkin transactions 1 
Abstract: Zinc bromide (ZnBr2) has proved to be a facile and efficient catalyst for the stereoselective semipinacol rearrangement of α-hydroxy epoxides at room temperature. Of note are the presence in the product of two adjacent chiral carbon centers, particularly the creation of a stereoselective quaternary center, and the efficient synthesis of β-hydroxy ketones, including some with naturally occurring spiroalkane skeletons. As an example of its application, important diastereomerically enriched spirbcyclic diol ligands have been synthesized conveniently via this rearrangement followed by reduction of the spirocyclic β-hydroxy ketones obtained with appropriate hydride reagents.
URI: http://hdl.handle.net/10397/25242
ISSN: 0300-922X
DOI: 10.1039/b006182o
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