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手性催化的烯丙醇及其衍生物的合成及其在有机合成中的应用。

Catalytic asymmetric synthesis of allylic alcohols and derivatives and their applications in organic synthesis.

机构信息

Institut für Organische Chemie und Biochemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg i. Brsg., Germany.

出版信息

Angew Chem Int Ed Engl. 2013 Feb 11;52(7):1890-932. doi: 10.1002/anie.201204579. Epub 2013 Jan 14.

Abstract

Allylic alcohols represent an important and highly versatile class of chiral building blocks for organic synthesis. This Review summarizes the plethora of methods developed for the catalytic asymmetric synthesis of enantioenriched allylic alcohols. These include: dynamic kinetic resolution (DKR/DKAT), nucleophilic 1,2-addition to carbonyl groups, allylic substitution, oxidation of C-H bonds, the addition of O nucleophiles to π systems, reduction of unsaturated carbonyl compounds, and an alternative route from enantioenriched propargylic alcohols. Furthermore, these catalytic asymmetric processes are exemplified by their applications in the syntheses of complex molecules such as natural products and potential therapeutic agents.

摘要

烯丙醇是有机合成中一类重要且用途广泛的手性砌块。本综述总结了大量用于催化不对称合成手性烯丙醇的方法。这些方法包括:动态动力学拆分(DKR/DKAT)、亲核 1,2-加成到羰基、烯丙基取代、C-H 键氧化、O 亲核试剂对π系统的加成、不饱和羰基化合物的还原以及从手性烯丙基丙醇的替代途径。此外,这些催化不对称过程通过它们在手性复杂分子如天然产物和潜在治疗剂的合成中的应用实例来证明。

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