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N-杂环卡宾催化的二氧吲哚与烯醛的氧化[3+2]环化反应：高烯醇盐与烯醇盐的交叉偶联

N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate.

作者信息

Chen Xiang-Yu, Chen Kun-Quan, Sun De-Qun, Ye Song

机构信息

Beijing National Laboratory for Molecular Sciences , CAS Key Laboratory of Molecular Recognition and Function , Institute of Chemistry , Chinese Academy of Sciences , Beijing 100190 , China . Email:

University of Chinese Academy of Sciences , Beijing 100049 , P. R. China.

出版信息

Chem Sci. 2017 Mar 1;8(3):1936-1941. doi: 10.1039/c6sc04135c. Epub 2016 Nov 9.

DOI:10.1039/c6sc04135c
PMID:28451308
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5384455/
Abstract

The N-heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindole and enals was developed, giving the corresponding spirocyclic oxindole-γ-lactones in good yields with high to excellent diastereo- and enantioselectivities. The challenging aliphatic enals worked effectively using this strategy. The oxidative cross coupling of homoenolate and enolate single electron transfer was proposed as the key step for the reaction.

摘要

开发了氮杂环卡宾催化的二氧吲哚与烯醛的氧化[3+2]环化反应，以良好的产率、高至优异的非对映和对映选择性得到相应的螺环氧化吲哚-γ-内酯。使用该策略，具有挑战性的脂肪族烯醛也能有效反应。提出了均烯醇盐和烯醇盐的氧化交叉偶联单电子转移作为该反应的关键步骤。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e2b3/5384455/15c04196511c/c6sc04135c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e2b3/5384455/420195386ff1/c6sc04135c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e2b3/5384455/887b667b4b17/c6sc04135c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e2b3/5384455/73559f726da8/c6sc04135c-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e2b3/5384455/dfdf842c7b73/c6sc04135c-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e2b3/5384455/15c04196511c/c6sc04135c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e2b3/5384455/420195386ff1/c6sc04135c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e2b3/5384455/887b667b4b17/c6sc04135c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e2b3/5384455/73559f726da8/c6sc04135c-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e2b3/5384455/dfdf842c7b73/c6sc04135c-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e2b3/5384455/15c04196511c/c6sc04135c-f1.jpg

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