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对映选择性布朗斯特酸催化的转移氢化反应：亚胺的有机催化还原

Enantioselective Brønsted acid catalyzed transfer hydrogenation: organocatalytic reduction of imines.

作者信息

Rueping Magnus, Sugiono Erli, Azap Cengiz, Theissmann Thomas, Bolte Michael

机构信息

Institute of Chemistry and Chemical Biology, Johann-Wolfgang Goethe University Frankfurt am Main, Marie-Curie-Strasse 11, D-60439 Frankfurt, Germany.

出版信息

Org Lett. 2005 Aug 18;7(17):3781-3. doi: 10.1021/ol0515964.

DOI:10.1021/ol0515964
PMID:16092874
Abstract

The first enantioselective Brønsted acid catalyzed reduction of imines has been developed. This new organocatalytic transfer hydrogenation of ketimines with Hantzsch dihydropyridine as the hydrogen source offers a mild method to various chiral amines with high enantioselectivity. The stereochemistry of the chiral amines can be rationalized by a stereochemical model derived from an X-ray crystal structure of a chiral BINOL phosphate catalyst. [reaction: see text]

摘要

首次实现了对映选择性布朗斯特酸催化的亚胺还原反应。这种以汉斯酯二氢吡啶为氢源的新型酮亚胺有机催化转移氢化反应，为制备各种具有高对映选择性的手性胺提供了一种温和的方法。手性胺的立体化学可以通过基于手性联萘酚磷酸酯催化剂的X射线晶体结构推导出来的立体化学模型进行合理解释。[反应：见正文]

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