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易于获得的9-表氨基金鸡纳生物碱衍生物可促进醛和酮与硝基烯烃的高效、高对映选择性加成反应。

Readily accessible 9-epi-amino cinchona alkaloid derivatives promote efficient, highly enantioselective additions of aldehydes and ketones to nitroolefins.

作者信息

McCooey Séamus H, Connon Stephen J

机构信息

Centre for Synthesis and Chemical Biology, School of Chemistry, University of Dublin, Trinity College, Dublin 2, Ireland.

出版信息

Org Lett. 2007 Feb 15;9(4):599-602. doi: 10.1021/ol0628006. Epub 2007 Jan 23.

Abstract

Simple cinchona alkaloid derivatives, available via a one-pot procedure from commercially available starting materials, have been shown to promote highly enantio- and diastereoselective Michael-type addition reactions between enolizable carbonyl compounds and nitroalkenes of broad scope. The influence of both the absolute and relative stereochemistry at C-9 on catalyst performance has also been assessed. [reaction: see text].

摘要

简单的金鸡纳生物碱衍生物可通过一锅法由市售起始原料制得,已证明其能促进可烯醇化羰基化合物与多种硝基烯烃之间的高度对映和非对映选择性迈克尔型加成反应。还评估了C-9位的绝对和相对立体化学对催化剂性能的影响。[反应:见正文]

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