Catalytic conjugate addition of acyl anion equivalents promoted by fluorodesilylation

Scott E. Denmark; Lindsey R. Cullen

doi:10.1021/ol403041k

Catalytic conjugate addition of acyl anion equivalents promoted by fluorodesilylation

Scott E. Denmark, Lindsey R. Cullen

Chemistry

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

Abstract

The conjugate addition of acyl anion equivalents derived from 2-silyl-1,3-dithianes to α,β-unsaturated ketones and esters has been achieved using a substoichiometric amount of TBAF. High yields and short reaction times are observed for the addition of aryl-1,3-dithianes to a variety of cyclic and acyclic α,β-unsaturated carbonyl acceptors. Observation of the reactive anion by ¹³C NMR spectroscopy and extension to an asymmetric variant is also presented.

Original language	English (US)
Pages (from-to)	70-73
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	1
DOIs	https://doi.org/10.1021/ol403041k
State	Published - Jan 3 2014

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol403041k

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abstract = "The conjugate addition of acyl anion equivalents derived from 2-silyl-1,3-dithianes to α,β-unsaturated ketones and esters has been achieved using a substoichiometric amount of TBAF. High yields and short reaction times are observed for the addition of aryl-1,3-dithianes to a variety of cyclic and acyclic α,β-unsaturated carbonyl acceptors. Observation of the reactive anion by 13C NMR spectroscopy and extension to an asymmetric variant is also presented.",

author = "Denmark, {Scott E.} and Cullen, {Lindsey R.}",

note = "Funding Information: * The data for this study were collected in collaboration with the Tianjin Academy of Social Sciences. We are grateful to the Academy and to President Wang Hui in particular for assistance. Jianhong Lin's research is partially supported by the Rhode Island College Faculty Research Fund.",

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doi = "10.1021/ol403041k",

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AU - Denmark, Scott E.

AU - Cullen, Lindsey R.

N1 - Funding Information: * The data for this study were collected in collaboration with the Tianjin Academy of Social Sciences. We are grateful to the Academy and to President Wang Hui in particular for assistance. Jianhong Lin's research is partially supported by the Rhode Island College Faculty Research Fund.

PY - 2014/1/3

Y1 - 2014/1/3

N2 - The conjugate addition of acyl anion equivalents derived from 2-silyl-1,3-dithianes to α,β-unsaturated ketones and esters has been achieved using a substoichiometric amount of TBAF. High yields and short reaction times are observed for the addition of aryl-1,3-dithianes to a variety of cyclic and acyclic α,β-unsaturated carbonyl acceptors. Observation of the reactive anion by 13C NMR spectroscopy and extension to an asymmetric variant is also presented.

AB - The conjugate addition of acyl anion equivalents derived from 2-silyl-1,3-dithianes to α,β-unsaturated ketones and esters has been achieved using a substoichiometric amount of TBAF. High yields and short reaction times are observed for the addition of aryl-1,3-dithianes to a variety of cyclic and acyclic α,β-unsaturated carbonyl acceptors. Observation of the reactive anion by 13C NMR spectroscopy and extension to an asymmetric variant is also presented.

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Catalytic conjugate addition of acyl anion equivalents promoted by fluorodesilylation

Abstract

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