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底物与碳-碳三键作为自由基受体的级联自由基反应。

Cascade radical reaction of substrates with a carbon-carbon triple bond as a radical acceptor.

机构信息

School of Pharmacy, Hyogo University of Health Sciences, Minatojima, Chuo-ku, Kobe 650-8530, Japan ; Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.

出版信息

Beilstein J Org Chem. 2013 Jun 13;9:1148-55. doi: 10.3762/bjoc.9.128. Print 2013.

DOI:10.3762/bjoc.9.128
PMID:23843907
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3701377/
Abstract

The limitation of hydroxamate ester as a chiral Lewis acid coordination moiety was first shown in an intermolecular reaction involving a radical addition and sequential allylation processes. Next, the effect of hydroxamate ester was studied in the cascade addition-cyclization-trapping reaction of substrates with a carbon-carbon triple bond as a radical acceptor. When substrates with a methacryloyl moiety and a carbon-carbon triple bond as two polarity-different radical acceptors were employed, the cascade reaction proceeded effectively. A high level of enantioselectivity was also obtained by a proper combination of chiral Lewis acid and these substrates.

摘要

羟胺酯作为手性路易斯酸配位部分的局限性首先在涉及自由基加成和连续烯丙基化过程的分子间反应中得到了证明。接下来，研究了羟胺酯在手性路易斯酸参与的底物与碳-碳三键作为自由基受体的加成-环化-捕获反应中的影响。当使用具有甲基丙烯酰基部分和碳-碳三键作为两个极性不同的自由基受体的底物时，级联反应有效地进行。通过手性路易斯酸和这些底物的适当组合，也获得了高水平的对映选择性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/2b472131527a/Beilstein_J_Org_Chem-09-1148-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/2e24ff349230/Beilstein_J_Org_Chem-09-1148-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/90f1e9d9a668/Beilstein_J_Org_Chem-09-1148-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/860ebe915607/Beilstein_J_Org_Chem-09-1148-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/992cc2c43b11/Beilstein_J_Org_Chem-09-1148-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/7c580b44c93e/Beilstein_J_Org_Chem-09-1148-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/9fad900922fb/Beilstein_J_Org_Chem-09-1148-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/cfd9d3a4cd80/Beilstein_J_Org_Chem-09-1148-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/7a93c3d1b5a8/Beilstein_J_Org_Chem-09-1148-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/99b23cb74d57/Beilstein_J_Org_Chem-09-1148-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/5a0bdc5de69a/Beilstein_J_Org_Chem-09-1148-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/b73904355968/Beilstein_J_Org_Chem-09-1148-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/2b472131527a/Beilstein_J_Org_Chem-09-1148-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/2e24ff349230/Beilstein_J_Org_Chem-09-1148-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/90f1e9d9a668/Beilstein_J_Org_Chem-09-1148-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/860ebe915607/Beilstein_J_Org_Chem-09-1148-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/992cc2c43b11/Beilstein_J_Org_Chem-09-1148-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/7c580b44c93e/Beilstein_J_Org_Chem-09-1148-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/9fad900922fb/Beilstein_J_Org_Chem-09-1148-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/cfd9d3a4cd80/Beilstein_J_Org_Chem-09-1148-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/7a93c3d1b5a8/Beilstein_J_Org_Chem-09-1148-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/99b23cb74d57/Beilstein_J_Org_Chem-09-1148-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/5a0bdc5de69a/Beilstein_J_Org_Chem-09-1148-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/b73904355968/Beilstein_J_Org_Chem-09-1148-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa5b/3701377/2b472131527a/Beilstein_J_Org_Chem-09-1148-g013.jpg

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