Understanding the Reactivity of Acyl Anion Equivalents: The Epoxide Ring Opening Case

Eger WA, Grange RL, Schill H, Goumont R, Clark T, Williams CM (2011)

Publication Status: Published

Publication Type: Journal article

Publication year: 2011

Journal

European Journal of Organic Chemistry Wiley-VCH Verlag

Publisher: Wiley-VCH Verlag

Pages Range: 2548-2553

Journal Issue: 13

DOI: 10.1002/ejoc.201001680

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.

Authors with CRIS profile

Timothy Clark Computer-Chemie-Centrum

Involved external institutions

University of Queensland AU Australia (AU) Versailles Saint-Quentin-en-Yvelines University / Université de Versailles Saint-Quentin-en-Yvelines (UVSQ) FR France (FR)

How to cite

APA:

Eger, W.A., Grange, R.L., Schill, H., Goumont, R., Clark, T., & Williams, C.M. (2011). Understanding the Reactivity of Acyl Anion Equivalents: The Epoxide Ring Opening Case. European Journal of Organic Chemistry, 13, 2548-2553. https://dx.doi.org/10.1002/ejoc.201001680

MLA:

Eger, Wilhelm A., et al. "Understanding the Reactivity of Acyl Anion Equivalents: The Epoxide Ring Opening Case." European Journal of Organic Chemistry 13 (2011): 2548-2553.

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