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烯基膦酸酯的催化不对称 Claisen 重排:相邻三级和全碳季碳中心的构建。

Catalytic asymmetric Claisen rearrangement of enolphosphonates: construction of vicinal tertiary and all-carbon quaternary centers.

机构信息

Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637, USA.

出版信息

Angew Chem Int Ed Engl. 2012 Aug 13;51(33):8264-7. doi: 10.1002/anie.201203092. Epub 2012 Jul 23.

DOI:10.1002/anie.201203092
PMID:22821885
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3517105/
Abstract

A Cu-catalyzed enantioselective Claisen rearrangement of easily-accessible enolphosphonates using commercially available ()-PhBOX as the chiral ligand was developed. A wide range of rearrangement products with contiguous tertiary and all carbon quaternary centers were obtained in excellent yields and stereoselectivities. The -ketophosphonate products could be easily transformed into other functional groups in high efficiency.

摘要

发展了一种使用商业可得的()-PhBOX 作为手性配体的 Cu 催化的对映选择性烯醇膦酸酯 Claisen重排反应。该反应能够以优异的收率和立体选择性得到具有连续叔碳和全碳季碳中心的广泛的重排产物。-酮膦酸酯产物可以高效地很容易转化为其他官能团。

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6
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