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^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

39 Citations (Scopus)

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.

Original language	English
Pages (from-to)	8751-8757
Number of pages	7
Journal	Tetrahedron
Volume	69
Issue number	41
DOIs	https://doi.org/10.1016/j.tet.2013.07.084
Publication status	Published - 2013 Oct 14

Keywords

Cascade Michael-aldol Oxindole Diastereoselectivity

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2013.07.084

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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. ",

year = "2013",

month = oct,

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doi = "10.1016/j.tet.2013.07.084",

language = "English",

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

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 930107: Experimental Crystal Structure Determination

CCDC 930108: Experimental Crystal Structure Determination

Cite this

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 930107: Experimental Crystal Structure Determination

CCDC 930108: Experimental Crystal Structure Determination

Cite this