高非对映选择性α-羟化 Fox 手性助剂酰胺烯醇化物与分子氧。

Highly diastereoselective alpha-hydroxylation of Fox chiral auxiliary-based amide enolates with molecular oxygen.

机构信息

Laboratoire Synthèse Organique Sélective et Chimie bioOrganique (SOSCO), Université de Cergy-Pontoise, 5 Mail Gay-Lussac 95000 Cergy-Pontoise Cedex, France.

出版信息

Org Lett. 2010 Apr 2;12(7):1496-9. doi: 10.1021/ol100211s.

DOI:10.1021/ol100211s

PMID:20218638

Abstract

Using a trifluoromethylated oxazolidine (Fox) chiral auxiliary, the hydroxylation reaction of enolates was very efficiently performed under smooth and friendly conditions with molecular oxygen as oxidizer. This reaction occurred with an extremely high diastereoselectivity. After cleavage, the chiral auxiliary is efficiently recovered and highly valuable enantiopure oxygenated carboxylic acids and alcohols are released.

摘要

利用三氟甲基化噁唑烷（Fox）手性助剂，在温和、友好的条件下，以分子氧为氧化剂，高效地进行烯醇化物的羟化反应。该反应具有极高的非对映选择性。拆分后，手性助剂可有效回收，得到高附加值的对映纯氧代羧酸和醇。