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催化对映选择性分子内氮杂-Diels-Alder 反应。

Catalytic enantioselective intramolecular aza-diels-alder reactions.

机构信息

Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, NJ 08854 (USA) http://seidel-group.com/

Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, NJ 08854 (USA) http://seidel-group.com/.

出版信息

Angew Chem Int Ed Engl. 2015 May 26;54(22):6608-12. doi: 10.1002/anie.201501536. Epub 2015 Apr 13.

Abstract

A readily available chiral Brønsted acid was identified as an efficient catalyst for intramolecular Povarov reactions. Polycyclic amines containing three contiguous stereogenic centers were obtained with excellent stereocontrol in a single step from secondary anilines and aldehydes possessing a pendent dienophile. These transformations constitute the first examples of catalytic enantioselective intramolecular aza-Diels-Alder reactions.

摘要

一种易得的手性布朗斯台德酸被鉴定为高效催化剂,可用于分子内 Povarov 反应。从具有烯丙二烯侧基的二级苯胺和醛出发,通过一步反应即可获得含有三个连续立体中心的多环胺,具有优异的立体选择性。这些转化构成了首例催化对映选择性分子内氮杂 Diels-Alder 反应的例子。

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