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全旋光性在分子内[2+2]环加成反应中的传递——炔丙基烯丙基酮的热[2+2]环加成反应生成非外消旋螺环氧化吲哚。

Complete transfer of chirality in an intramolecular, thermal [2 + 2] cycloaddition of allene-ynes to form non-racemic spirooxindoles.

机构信息

University of Pittsburgh, Department of Chemistry, Chevron Science Center, 219 Parkman Avenue, Pittsburgh, PA 15260, USA.

出版信息

Beilstein J Org Chem. 2011;7:601-5. doi: 10.3762/bjoc.7.70. Epub 2011 May 12.

DOI:10.3762/bjoc.7.70
PMID:21647261
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3107521/
Abstract

A thermal [2 + 2] cycloaddition reaction of allene-ynes has been used to transform chiral non-racemic allenyl oxindoles into chiral non-racemic spirooxindoles containing an alkylidene cyclobutene moiety. The enantiomeric excesses were determined by chiral lanthanide shift NMR analysis and the transfer of chiral information from the allene to the spirooxindole was found to be greater than 95%.

摘要

烯丙基炔的热[2+2]环加成反应已被用于将手性非外消旋的烯丙基氧吲哚转化为含有亚烷基环丁烯部分的手性非外消旋螺环氧化吲哚。对映过量通过手性镧系元素位移 NMR 分析确定，并且发现从烯丙基到螺环氧化吲哚的手性信息转移大于 95%。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/549a/3107521/07fa95d18b45/Beilstein_J_Org_Chem-07-601-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/549a/3107521/7dfbaa23bf41/Beilstein_J_Org_Chem-07-601-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/549a/3107521/2a86f8f656b9/Beilstein_J_Org_Chem-07-601-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/549a/3107521/e1ced2035770/Beilstein_J_Org_Chem-07-601-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/549a/3107521/c50c0d5fb0e8/Beilstein_J_Org_Chem-07-601-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/549a/3107521/e43bd7bf05e4/Beilstein_J_Org_Chem-07-601-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/549a/3107521/6643a329a5dc/Beilstein_J_Org_Chem-07-601-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/549a/3107521/07fa95d18b45/Beilstein_J_Org_Chem-07-601-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/549a/3107521/7dfbaa23bf41/Beilstein_J_Org_Chem-07-601-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/549a/3107521/2a86f8f656b9/Beilstein_J_Org_Chem-07-601-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/549a/3107521/e1ced2035770/Beilstein_J_Org_Chem-07-601-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/549a/3107521/c50c0d5fb0e8/Beilstein_J_Org_Chem-07-601-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/549a/3107521/e43bd7bf05e4/Beilstein_J_Org_Chem-07-601-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/549a/3107521/6643a329a5dc/Beilstein_J_Org_Chem-07-601-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/549a/3107521/07fa95d18b45/Beilstein_J_Org_Chem-07-601-g005.jpg

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本文引用的文献

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Core-structure-motivated design of a phosphine-catalyzed [3+2] cycloaddition reaction: enantioselective syntheses of spirocyclopenteneoxindoles.基于核心结构的膦催化[3+2]环加成反应设计：手性螺环戊烯氧吲哚的对映选择性合成。
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