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对映选择性和非对映选择性的有机催化硝基烷烃与烯酮二酯的共轭加成反应。

Enantio- and Diastereoselective Organocatalytic Conjugate Additions of Nitroalkanes to Enone Diesters.

机构信息

Department of Chemistry, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599, United States.

出版信息

Org Lett. 2017 Nov 3;19(21):5783-5785. doi: 10.1021/acs.orglett.7b02735.

DOI:10.1021/acs.orglett.7b02735
PMID:29035548
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5669806/
Abstract

Enantio- and diastereoselective conjugate addition reactions between nitroethane or nitropropane and enone diesters are reported. A bifunctional triaryliminophosphorane catalyzed the addition reaction with consistently excellent stereoselectivities and yields across a wide range of substrates. By the use of the gem-diester functional handle present in the adducts, local desymmetrization via diastereotopic group discrimination was demonstrated, and a polyfunctionalized lactam with three contiguous stereocenters was synthesized.

摘要

手性和非对映选择性共轭加成反应硝基乙烷或硝基丙烷和烯酮二酯之间的报道。双功能三芳基亚膦催化加成反应具有一致的优异的立体选择性和产量在广泛的底物。通过使用加合物中存在的双酯官能团，通过非对映体基团的立体选择识别实现了局部去对称化，并合成了具有三个连续立体中心的多官能化内酰胺。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b0e3/5669806/f8805922e669/nihms913609f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b0e3/5669806/e5f8d944076b/nihms913609f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b0e3/5669806/73d0459402ad/nihms913609f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b0e3/5669806/921fbeace7fd/nihms913609f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b0e3/5669806/e81f86588b2f/nihms913609f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b0e3/5669806/f8805922e669/nihms913609f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b0e3/5669806/e5f8d944076b/nihms913609f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b0e3/5669806/73d0459402ad/nihms913609f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b0e3/5669806/921fbeace7fd/nihms913609f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b0e3/5669806/e81f86588b2f/nihms913609f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b0e3/5669806/f8805922e669/nihms913609f5.jpg

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