Understanding the reactivity of acyl anion equivalents: the epoxide ring opening case

W. Eger; R. Grange; H. Schill; R. Goumont; Tim Clark; C. Williams

doi:10.1002/ejoc.201001680

Understanding the reactivity of acyl anion equivalents: the epoxide ring opening case

W. Eger, R. Grange, H. Schill, R. Goumont, Tim Clark, C. Williams

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

Abstract

Acyl anion equivalents (umpolung) are the practitioner's first choice en route to 1,3-hydroxy keto compounds from epoxides. Why? This investigation evaluates computationally and experimentally the reactivity of a near comprehensive range of acyl anion equivalents using epoxide ring opening as a test vehicle. Reactivity understanding, reactivity order, surprise failures in performance, along with unprecedented, but far from superior, reactivity of TosMIC is presented for the first time.

Original language	English
Pages (from-to)	2548-2553
Number of pages	6
Journal	European Journal of Organic Chemistry
Volume	2011
Issue number	3
DOIs	https://doi.org/10.1002/ejoc.201001680
Publication status	Published - May 2011

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title = "Understanding the reactivity of acyl anion equivalents: the epoxide ring opening case",

abstract = "Acyl anion equivalents (umpolung) are the practitioner's first choice en route to 1,3-hydroxy keto compounds from epoxides. Why? This investigation evaluates computationally and experimentally the reactivity of a near comprehensive range of acyl anion equivalents using epoxide ring opening as a test vehicle. Reactivity understanding, reactivity order, surprise failures in performance, along with unprecedented, but far from superior, reactivity of TosMIC is presented for the first time.",

author = "W. Eger and R. Grange and H. Schill and R. Goumont and Tim Clark and C. Williams",

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AU - Eger, W.

AU - Grange, R.

AU - Schill, H.

AU - Goumont, R.

AU - Clark, Tim

AU - Williams, C.

PY - 2011/5

Y1 - 2011/5

N2 - Acyl anion equivalents (umpolung) are the practitioner's first choice en route to 1,3-hydroxy keto compounds from epoxides. Why? This investigation evaluates computationally and experimentally the reactivity of a near comprehensive range of acyl anion equivalents using epoxide ring opening as a test vehicle. Reactivity understanding, reactivity order, surprise failures in performance, along with unprecedented, but far from superior, reactivity of TosMIC is presented for the first time.

AB - Acyl anion equivalents (umpolung) are the practitioner's first choice en route to 1,3-hydroxy keto compounds from epoxides. Why? This investigation evaluates computationally and experimentally the reactivity of a near comprehensive range of acyl anion equivalents using epoxide ring opening as a test vehicle. Reactivity understanding, reactivity order, surprise failures in performance, along with unprecedented, but far from superior, reactivity of TosMIC is presented for the first time.

U2 - 10.1002/ejoc.201001680

DO - 10.1002/ejoc.201001680

M3 - Article

SN - 1434-193X

VL - 2011

SP - 2548

EP - 2553

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 3

ER -

Understanding the reactivity of acyl anion equivalents: the epoxide ring opening case

Abstract

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