Elsevier

Tetrahedron Letters

Volume 54, Issue 33, 14 August 2013, Pages 4487-4490
Tetrahedron Letters

TiCl4 mediated preparation of (E)-non-conjugated homoallylic alcohols with α-substituted allylsilanes

https://doi.org/10.1016/j.tetlet.2013.06.047Get rights and content

Abstract

The allylation of various aldehydes with α-substituted allylsilanes in the presence of TiCl4 has been investigated. It has been shown that these reagents readily allow for good yields and high to excellent diastereoselectivities (up to >20:1) for a series of aldehydes, thereby providing a means of preparing non-conjugated (E)-homoallylic alcohols in a single step.

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Acknowledgments

Support for this project was provided by the University of Alabama and in part the National Science Foundation CAREER program under CHE-0845011.

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