Sequential Visible-Light and N-Heterocyclic Carbene Catalysis: Stereoselective Synthesis of Tetrahydropyrano[2,3-b]indoles

An efficiently stereoselective [4 + 2] cycloaddition of 3-alkylenyloxindoles and a-diazoketones through sequential visible-light photoactivation and N-heterocyclic carbene catalysis was achieved. A series of tetrahydropyrano[2,3-b]indoles with an all-carbon quaternary stereocenter were obtained in g...

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Published inOrganic letters Vol. 22; no. 11; pp. 4440 - 4443
Main Authors Wang, Chengyuan, Wang, Zheyuan, Yang, Jin, Shi, Shi-Hui, Hui, Xin-Ping
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 05.06.2020
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SYSTEM
HIGHLY ENANTIOSELECTIVE SYNTHESIS
ROUTE
ASYMMETRIC-SYNTHESIS
KETENES
4+2 CYCLOADDITION
AMINES
ACID COOPERATIVE CATALYSIS
BETA-LACTONES
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Summary:An efficiently stereoselective [4 + 2] cycloaddition of 3-alkylenyloxindoles and a-diazoketones through sequential visible-light photoactivation and N-heterocyclic carbene catalysis was achieved. A series of tetrahydropyrano[2,3-b]indoles with an all-carbon quaternary stereocenter were obtained in good yields with excellent diastereo- and enantioselectivities.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01447