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对甲苯磺酰肼促进的3-苯亚甲基氧化吲哚与双螺环戊烷双氧化吲哚衍生物的自共轭还原-迈克尔/羟醛反应

Tosylhydrazine-promoted self-conjugate reduction-Michael/aldol reaction of 3-phenacylideneoxindoles towards dispirocyclopentanebisoxindole derivatives.

作者信息

Pramanik Sayan, Mukhopadhyay Chhanda

机构信息

Department of Chemistry, University of Calcutta, 92 APC Road, Kolkata-700009, India.

出版信息

Beilstein J Org Chem. 2022 Apr 27;18:469-478. doi: 10.3762/bjoc.18.49. eCollection 2022.

DOI:10.3762/bjoc.18.49
PMID:35558650
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9062653/
Abstract

An efficient tosylhydrazine-mediated conjugate reduction of 3-phenacylideneoxindole and sequential Michael/intramolecular aldol reaction is reported under base-catalyzed conditions towards the formation of densely substituted dispirocyclopentanebisoxindole derivatives. The reaction proceeded in a diastereoselective manner to afford four chiral stereocenters. The method also has advantages of wide substrate scope, readily available starting materials and operational simplicity through one pot reaction.

摘要

报道了在碱催化条件下，通过高效的对甲苯磺酰肼介导的3-苯亚甲基氧化吲哚共轭还原以及随后的迈克尔/分子内羟醛反应，形成高度取代的双螺环戊烷并双氧化吲哚衍生物。该反应以非对映选择性方式进行，得到四个手性立体中心。该方法还具有底物范围广、起始原料容易获得以及通过一锅反应操作简单的优点。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/682a/9062653/8263e67350c4/Beilstein_J_Org_Chem-18-469-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/682a/9062653/028ad43569df/Beilstein_J_Org_Chem-18-469-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/682a/9062653/0dc26287df6f/Beilstein_J_Org_Chem-18-469-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/682a/9062653/bcb654538693/Beilstein_J_Org_Chem-18-469-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/682a/9062653/8df05c4f7175/Beilstein_J_Org_Chem-18-469-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/682a/9062653/460e5439e71b/Beilstein_J_Org_Chem-18-469-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/682a/9062653/24adf93ba67a/Beilstein_J_Org_Chem-18-469-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/682a/9062653/e7c9ed76d3bb/Beilstein_J_Org_Chem-18-469-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/682a/9062653/3a83e73ead98/Beilstein_J_Org_Chem-18-469-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/682a/9062653/8263e67350c4/Beilstein_J_Org_Chem-18-469-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/682a/9062653/028ad43569df/Beilstein_J_Org_Chem-18-469-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/682a/9062653/0dc26287df6f/Beilstein_J_Org_Chem-18-469-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/682a/9062653/bcb654538693/Beilstein_J_Org_Chem-18-469-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/682a/9062653/8df05c4f7175/Beilstein_J_Org_Chem-18-469-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/682a/9062653/460e5439e71b/Beilstein_J_Org_Chem-18-469-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/682a/9062653/24adf93ba67a/Beilstein_J_Org_Chem-18-469-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/682a/9062653/e7c9ed76d3bb/Beilstein_J_Org_Chem-18-469-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/682a/9062653/3a83e73ead98/Beilstein_J_Org_Chem-18-469-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/682a/9062653/8263e67350c4/Beilstein_J_Org_Chem-18-469-g010.jpg

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