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Highly Stereoselective 2-Oxonia-Cope Rearrangement: A Platform Enabling At-Will Control of Regio-, Enantio-, and Diastereoselectivity in the Vinylogous Aldol Reactions of Aldehydes
Organic Letters ( IF 5.2 ) Pub Date : 2018-01-18 00:00:00 , DOI: 10.1021/acs.orglett.7b03895
Akhil Padarti 1 , Dongeun Kim 1 , Hyunsoo Han 1
Affiliation  

A distinctly different approach for the vinylogous aldolation of aldehydes is described, which exploits 2-oxonia-Cope rearrangement reactions between two readily available partners, a set of rationally designed chiral homoallylic alcohol synthons and aldehydes, under simple conditions. In these processes, chirality transfer from the former to the latter is nearly perfect, giving rise to excellent enantio- and diastereoselectivity without the regioselectivity issue associated with traditional vinylogous aldol reactions.

中文翻译:

高度立体选择性2-Oxonia-Cope重排:能够在全醛控制醛的乙烯基醛醇醛反应中区域,对映体和非对映选择性的平台。

描述了一种用于乙烯醇醛缩醛醛的截然不同的方法,其在简单条件下利用了两个容易获得的伙伴,一组合理设计的手性均烯丙基醇合成子和醛之间的2-氧代-Cope重排反应。在这些过程中,手性从前者向后者的转移几乎是完美的,从而产生了出色的对映异构和非对映异构选择性,而没有与传统的乙烯基醛醇缩合反应相关的区域选择性问题。
更新日期:2018-01-18
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