Highly Chemoselective Calcium‐Catalyzed Propargylic Deoxygenation
- 29 February 2012
- journal article
- Published by Wiley in Chemistry – A European Journal
- Vol. 18 (15), 4687-4691
- https://doi.org/10.1002/chem.201103691
Abstract
A calcium‐catalyzed direct reduction of propargylic alcohols and ethers has been accomplished by using triethylsilane as a nucleophilic hydride source. At room temperature a variety of secondary propargylic alcohols was deoxygenated to the corresponding hydrocarbons in excellent yields. Furthermore, for the first time, a catalytic deoxygenation of tertiary propargylic alcohols was generally applicable. The same protocol was suitable for an efficient reduction of secondary as well as tertiary propargylic methyl, benzyl and allyl ethers. Substrates containing an additional keto‐, ester or secondary hydroxyl function were reduced with exceptional chemoselectivity at the propargylic position.This publication has 49 references indexed in Scilit:
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