Journal
ORGANIC LETTERS
Volume 7, Issue 15, Pages 3227-3230Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol051030f
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The Lewis base-catalyzed additions of alkynyl nucleophiles to aldehydes, ketones, and imines is described. Mechanistic studies strongly indicate that the use of new triethoxysilylalkynes facilitates access of a reactive hypervalent silicate intermediate. This activated carbon nucleophile subsequently undergoes rapid addition to carbonyl compounds and imines, thus affording the secondary and tertiary propargyl systems in moderate to high yield.
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