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可见光介导的脱氧反应合成手性四氢呋喃和吡咯烷

Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible-Light-Mediated Deoxygenation.

作者信息

Rackl Daniel, Kais Viktor, Lutsker Eugen, Reiser And Oliver

机构信息

Institute of Organic Chemistry University of Regensburg 93053 Regensburg Germany.

出版信息

European J Org Chem. 2017 Apr 18;2017(15):2130-2138. doi: 10.1002/ejoc.201700014. Epub 2017 Feb 28.

DOI:10.1002/ejoc.201700014
PMID:28529446
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5412674/
Abstract

The synthesis of chiral tetrahydrofurans and pyrrolidines starting from 1,2-diols or β-amino alcohols, respectively, by visible-light-mediated deoxygenation is described. Easily accessible monoallylated/propargylated substrates were activated either as inexpensive ethyl oxalates or as recyclable 3,5-bis(trifluoromethyl)benzoates to generate alkyl radicals suitable for 5--/5-- cyclizations under visible-light irradiation.

摘要

描述了分别从1,2 -二醇或β -氨基醇开始，通过可见光介导的脱氧反应合成手性四氢呋喃和吡咯烷。易于获得的单烯丙基化/炔丙基化底物可作为廉价的草酸乙酯或可回收的3,5 -双（三氟甲基）苯甲酸酯被活化，以产生适合在可见光照射下进行5 - /5 - 环化反应的烷基自由基。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b01b/5412674/83df9db95c48/EJOC-2017-2130-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b01b/5412674/54e68a8aede4/EJOC-2017-2130-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b01b/5412674/a625005ce15e/EJOC-2017-2130-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b01b/5412674/6bfcbef40d0f/EJOC-2017-2130-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b01b/5412674/a38e92c99825/EJOC-2017-2130-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b01b/5412674/bc4401ef30c8/EJOC-2017-2130-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b01b/5412674/83df9db95c48/EJOC-2017-2130-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b01b/5412674/54e68a8aede4/EJOC-2017-2130-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b01b/5412674/a625005ce15e/EJOC-2017-2130-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b01b/5412674/6bfcbef40d0f/EJOC-2017-2130-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b01b/5412674/a38e92c99825/EJOC-2017-2130-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b01b/5412674/bc4401ef30c8/EJOC-2017-2130-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b01b/5412674/83df9db95c48/EJOC-2017-2130-g007.jpg

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