Organocatalytic formal [5+1] annulation: Diastereoselective cascade synthesis of functionalized six-membered spirocyclic indane-1,3-diones/oxindoles via Michael-aldol reaction

Suparna Roy; Mamatha Amireddy; Kwunmin Chen

doi:10.1016/j.tet.2013.07.084

Organocatalytic formal [5+1] annulation: Diastereoselective cascade synthesis of functionalized six-membered spirocyclic indane-1,3-diones/oxindoles via Michael-aldol reaction

Suparna Roy
, Mamatha Amireddy
, Kwunmin Chen^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

40 引文斯高帕斯（Scopus）

摘要

An efficient cascade protocol has been developed for the diastereoselective synthesis of functionalized six-membered spirocyclic compounds. The reaction proceeded smoothly between indane 1,3-diones/oxindoles/coumaranone as the dinucleophilic components and (E)-5-nitro-6-aryl-hex-5-en-2-one as the dielectrophile to give the desired products with reasonable to high chemical yields (30-84%) and high levels of diastereoselectivities (upto >95:5 dr). The reaction proceeded smoothly via cascade Michael-aldol reaction.

原文	英語
頁（從 - 到）	8751-8757
頁數	7
期刊	Tetrahedron
卷	69
發行號	41
DOIs	https://doi.org/10.1016/j.tet.2013.07.084
出版狀態	已發佈 - 2013 10月 14

ASJC Scopus subject areas

生物化學
藥物發現
有機化學

存取文件

10.1016/j.tet.2013.07.084

其它文件與鏈接

CCDC 930108: Experimental Crystal Structure Determination
Roy, S. (Creator), Amireddy, M. (Creator) & Chen, K. (Creator), Unknown Publisher, 2013
DOI: 10.5517/cc106vhk, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc106vhk&sid=DataCite
資料集: Dataset
CCDC 930107: Experimental Crystal Structure Determination
Roy, S. (Creator), Amireddy, M. (Creator) & Chen, K. (Creator), Unknown Publisher, 2013
DOI: 10.5517/cc106vgj, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc106vgj&sid=DataCite
資料集: Dataset

引用此

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title = "Organocatalytic formal [5+1] annulation: Diastereoselective cascade synthesis of functionalized six-membered spirocyclic indane-1,3-diones/oxindoles via Michael-aldol reaction",

abstract = "An efficient cascade protocol has been developed for the diastereoselective synthesis of functionalized six-membered spirocyclic compounds. The reaction proceeded smoothly between indane 1,3-diones/oxindoles/coumaranone as the dinucleophilic components and (E)-5-nitro-6-aryl-hex-5-en-2-one as the dielectrophile to give the desired products with reasonable to high chemical yields (30-84\%) and high levels of diastereoselectivities (upto >95:5 dr). The reaction proceeded smoothly via cascade Michael-aldol reaction.",

keywords = "Cascade Michael-aldol Oxindole Diastereoselectivity",

author = "Suparna Roy and Mamatha Amireddy and Kwunmin Chen",

note = "Funding Information: We thank the National Science Council of the Republic of China (NSC 99-2113-M-003-002-MY3 ) for its financial support of our work. Our gratitude extends to the Academic Paper Editing Clinic at NTNU. ",

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AU - Roy, Suparna

AU - Amireddy, Mamatha

AU - Chen, Kwunmin

N1 - Funding Information: We thank the National Science Council of the Republic of China (NSC 99-2113-M-003-002-MY3 ) for its financial support of our work. Our gratitude extends to the Academic Paper Editing Clinic at NTNU.

PY - 2013/10/14

Y1 - 2013/10/14

N2 - An efficient cascade protocol has been developed for the diastereoselective synthesis of functionalized six-membered spirocyclic compounds. The reaction proceeded smoothly between indane 1,3-diones/oxindoles/coumaranone as the dinucleophilic components and (E)-5-nitro-6-aryl-hex-5-en-2-one as the dielectrophile to give the desired products with reasonable to high chemical yields (30-84%) and high levels of diastereoselectivities (upto >95:5 dr). The reaction proceeded smoothly via cascade Michael-aldol reaction.

AB - An efficient cascade protocol has been developed for the diastereoselective synthesis of functionalized six-membered spirocyclic compounds. The reaction proceeded smoothly between indane 1,3-diones/oxindoles/coumaranone as the dinucleophilic components and (E)-5-nitro-6-aryl-hex-5-en-2-one as the dielectrophile to give the desired products with reasonable to high chemical yields (30-84%) and high levels of diastereoselectivities (upto >95:5 dr). The reaction proceeded smoothly via cascade Michael-aldol reaction.

KW - Cascade Michael-aldol Oxindole Diastereoselectivity

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UR - https://www.scopus.com/pages/publications/84883195511#tab=citedBy

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Organocatalytic formal [5+1] annulation: Diastereoselective cascade synthesis of functionalized six-membered spirocyclic indane-1,3-diones/oxindoles via Michael-aldol reaction

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 930108: Experimental Crystal Structure Determination

CCDC 930107: Experimental Crystal Structure Determination

引用此