Lewis base-catalyzed additions of alkynes using trialkoxysilylalkynes

Robert B. Lettan; Karl A Scheidt

doi:10.1021/ol051030f

Lewis base-catalyzed additions of alkynes using trialkoxysilylalkynes

Robert B. Lettan, Karl A Scheidt^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

73 Scopus citations

Abstract

(Chemical Equation Presented) 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.

Original language	English (US)
Pages (from-to)	3227-3230
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	15
DOIs	https://doi.org/10.1021/ol051030f
State	Published - Jul 21 2005

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol051030f

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title = "Lewis base-catalyzed additions of alkynes using trialkoxysilylalkynes",

abstract = "(Chemical Equation Presented) 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.",

author = "Lettan, {Robert B.} and Scheidt, {Karl A}",

year = "2005",

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doi = "10.1021/ol051030f",

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T1 - Lewis base-catalyzed additions of alkynes using trialkoxysilylalkynes

AU - Lettan, Robert B.

AU - Scheidt, Karl A

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N2 - (Chemical Equation Presented) 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.

AB - (Chemical Equation Presented) 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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JO - Organic Letters

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ER -

Lewis base-catalyzed additions of alkynes using trialkoxysilylalkynes

Abstract

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