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

作者：Eger Wilhelm A; Grange Rebecca L; Schill Heiko; Goumont Regis; Clark Timothy; Williams Craig M^*

来源：European Journal of Organic Chemistry, 2011, 2011(13): 2548-2553.

DOI：10.1002/ejoc.201001680

• Umpolung
• Epoxides
• Acyl anion equivalent
• Carbonyl equivalent

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.

• 出版日期2011-5