Modulating the stereochemical outcome of the Ireland-Claisen reaction of (E)- and (Z)-allylic glycolates

Ken S. Feldman; Brandon R. Selfridge

doi:10.1016/j.tetlet.2011.12.011

Modulating the stereochemical outcome of the Ireland-Claisen reaction of (E)- and (Z)-allylic glycolates

Ken S. Feldman, Brandon R. Selfridge

Chemistry

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

10 Scopus citations

Abstract

The diastereoselectivity of Ireland-Claisen rearrangements of allylic glycolates is dependent on the E:Z ratio of the silyl ketene acetals, the alkene geometry in the allyl unit, and the transition state topography. High yields and excellent diastereoselectivities (>95:5) have been achieved for selected substrates, including those with R ₂ = ethyl that results in a newly formed quaternary center. A discussion of the scope, selectivities, and transition state models will be presented.

Original language	English (US)
Pages (from-to)	825-828
Number of pages	4
Journal	Tetrahedron Letters
Volume	53
Issue number	7
DOIs	https://doi.org/10.1016/j.tetlet.2011.12.011
State	Published - Feb 15 2012

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "The diastereoselectivity of Ireland-Claisen rearrangements of allylic glycolates is dependent on the E:Z ratio of the silyl ketene acetals, the alkene geometry in the allyl unit, and the transition state topography. High yields and excellent diastereoselectivities (>95:5) have been achieved for selected substrates, including those with R 2 = ethyl that results in a newly formed quaternary center. A discussion of the scope, selectivities, and transition state models will be presented.",

author = "Feldman, \{Ken S.\} and Selfridge, \{Brandon R.\}",

note = "Funding Information: Financial support from the National Science Foundation ( CHE 0956458 ) is gratefully acknowledged. ",

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AU - Feldman, Ken S.

AU - Selfridge, Brandon R.

N1 - Funding Information: Financial support from the National Science Foundation ( CHE 0956458 ) is gratefully acknowledged.

PY - 2012/2/15

Y1 - 2012/2/15

N2 - The diastereoselectivity of Ireland-Claisen rearrangements of allylic glycolates is dependent on the E:Z ratio of the silyl ketene acetals, the alkene geometry in the allyl unit, and the transition state topography. High yields and excellent diastereoselectivities (>95:5) have been achieved for selected substrates, including those with R 2 = ethyl that results in a newly formed quaternary center. A discussion of the scope, selectivities, and transition state models will be presented.

AB - The diastereoselectivity of Ireland-Claisen rearrangements of allylic glycolates is dependent on the E:Z ratio of the silyl ketene acetals, the alkene geometry in the allyl unit, and the transition state topography. High yields and excellent diastereoselectivities (>95:5) have been achieved for selected substrates, including those with R 2 = ethyl that results in a newly formed quaternary center. A discussion of the scope, selectivities, and transition state models will be presented.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 7

ER -

Modulating the stereochemical outcome of the Ireland-Claisen reaction of (E)- and (Z)-allylic glycolates

Abstract

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