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

Eger, Wilhelm A., Grange, Rebecca L, Schill, Heiko, Goumont, Régis, Clark, Timothy and Williams, Craig M. (2011) Understanding the reactivity of acyl anion equivalents: The epoxide ring opening case. European Journal of Organic Chemistry, 13: 2548-2553. doi:10.1002/ejoc.201001680


Author Eger, Wilhelm A.
Grange, Rebecca L
Schill, Heiko
Goumont, Régis
Clark, Timothy
Williams, Craig M.
Title Understanding the reactivity of acyl anion equivalents: The epoxide ring opening case
Journal name European Journal of Organic Chemistry   Check publisher's open access policy
ISSN 1434-193X
1099-0690
Publication date 2011-05
Sub-type Article (original research)
DOI 10.1002/ejoc.201001680
Issue 13
Start page 2548
End page 2553
Total pages 6
Place of publication Weinheim, Germany
Publisher Wiley
Collection year 2012
Language eng
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. Acyl anion equivalents are the practitioner's first choice en route to 1,3-hydroxy keto compounds from epoxides. This investigation evaluates 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 fromsuperior, reactivity of TosMIC is presented.
Keyword Umpolung
Epoxides
Acyl anion equivalent
Carbonyl equivalent
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ
Additional Notes Article first published online: 17 March 2011

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2012 Collection
School of Chemistry and Molecular Biosciences
 
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Created: Fri, 17 Feb 2012, 11:12:43 EST by Lucy O'Brien on behalf of School of Chemistry & Molecular Biosciences