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作为手性布朗斯特碱催化剂的氮杂环卡宾：一种高度非对映和对映选择性的1,6-加成反应。

N-Heterocyclic carbenes as chiral Brønsted base catalysts: a highly diastereo- and enantioselective 1,6-addition reaction.

作者信息

Santra Surojit, Porey Arka, Jana Barun, Guin Joyram

机构信息

Department of Organic Chemistry , Indian Association for the Cultivation of Science , 2A & 2B Raja S. C. Mullick Road, Jadavpur , Kolkata-700032 , India . Email:

出版信息

Chem Sci. 2018 Jul 2;9(30):6446-6450. doi: 10.1039/c8sc02138d. eCollection 2018 Aug 14.

DOI:10.1039/c8sc02138d
PMID:30288232
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6144034/
Abstract

Highly diastereo- and enantioselective 1,6-addition of 1,3-ketoamides to -quinone methides (-QMs) using chiral NHCs as Brønsted base catalysts is developed. The reaction is based on the utilization of a 1,3-ketoamide having acidic N-H that forms a chiral ion-pair consisting of the enolate and the azolium ion. Different β-ketoamides and functionalized -QMs are applicable to the reaction. Synthetic application of the method is demonstrated the preparation of highly enantioenriched β and γ-lactam derivatives.

摘要

开发了一种使用手性N-杂环卡宾作为布朗斯特碱催化剂，将1,3-酮酰胺高度非对映选择性和对映选择性地加成到醌甲基化物（-QMs）上的方法。该反应基于利用具有酸性N-H的1,3-酮酰胺，其形成由烯醇盐和唑鎓离子组成的手性离子对。不同的β-酮酰胺和功能化的-QMs适用于该反应。通过制备高度对映体富集的β和γ-内酰胺衍生物证明了该方法的合成应用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dc88/6144034/a99617f38e4a/c8sc02138d-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dc88/6144034/6cfb14f10408/c8sc02138d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dc88/6144034/842706289050/c8sc02138d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dc88/6144034/a02d98aecb20/c8sc02138d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dc88/6144034/a99617f38e4a/c8sc02138d-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dc88/6144034/6cfb14f10408/c8sc02138d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dc88/6144034/842706289050/c8sc02138d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dc88/6144034/a02d98aecb20/c8sc02138d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dc88/6144034/a99617f38e4a/c8sc02138d-f1.jpg

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