Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.
J Am Chem Soc. 2010 Mar 17;132(10):3268-9. doi: 10.1021/ja100161d.
An enantioselective method for the synthesis of beta-fluoroalcohols by catalytic nucleophilic fluorination of epoxides is described. Mild reaction conditions and high selectivity are made possible by the use of benzoyl fluoride as a soluble, latent source of fluoride anion. A chiral amine and chiral Lewis acid serve as cooperative catalysts for desymmetrizations of five- through eight-membered cyclic epoxides, affording products in up to 95% ee. The cocatalytic protocol is also effective for kinetic resolutions of racemic terminal epoxides, which proceed with k(rel) values as high as 300.
描述了一种通过环氧化合物的催化亲核氟化反应来合成β-氟醇的对映选择性方法。使用苯甲酰氟作为可溶性的、潜在的氟阴离子源，可以实现温和的反应条件和高选择性。手性胺和手性路易斯酸作为协同催化剂，用于五到八元环环氧的去对称化反应，产物的对映体过量值高达 95%。共催化方案对于外消旋末端环氧的动力学拆分也是有效的，其 k(rel)值高达 300。
