Carbene-Catalyzed Reaction of Indolyl Methylenemalononitriles and Enals for Access to Complex Tetrahydrocarbazoles

Chengli Mou; Liejin Zhou; Runjiang Song; Huifang Chai; Lin Hao; Yonggui Robin Chi

doi:10.1021/acs.orglett.0c00418

Carbene-Catalyzed Reaction of Indolyl Methylenemalononitriles and Enals for Access to Complex Tetrahydrocarbazoles

Chengli Mou, Liejin Zhou, Runjiang Song, Huifang Chai^*, Lin Hao, Yonggui Robin Chi

^*Corresponding author for this work

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

21 Citations (Scopus)

Abstract

A carbene-catalyzed enantioselective cascade reaction of substituted methylenemalononitriles and α-bromoenals is disclosed. Key steps of this cascade process include a formal [4 + 2] cycloaddition, aldol reaction, and intramolecular lactonization. Our reaction offers streamlined and highly stereoselective access to complex tetrahydrocarbazole derivatives, with simultaneous formation of four chemical bonds and four chiral centers.

Original language	English
Pages (from-to)	2542-2547
Number of pages	6
Journal	Organic Letters
Volume	22
Issue number	7
DOIs	https://doi.org/10.1021/acs.orglett.0c00418
Publication status	Published - Apr 3 2020
Externally published	Yes

Bibliographical note

Publisher Copyright:
Copyright © 2020 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "A carbene-catalyzed enantioselective cascade reaction of substituted methylenemalononitriles and α-bromoenals is disclosed. Key steps of this cascade process include a formal [4 + 2] cycloaddition, aldol reaction, and intramolecular lactonization. Our reaction offers streamlined and highly stereoselective access to complex tetrahydrocarbazole derivatives, with simultaneous formation of four chemical bonds and four chiral centers.",

author = "Chengli Mou and Liejin Zhou and Runjiang Song and Huifang Chai and Lin Hao and Chi, {Yonggui Robin}",

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doi = "10.1021/acs.orglett.0c00418",

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T1 - Carbene-Catalyzed Reaction of Indolyl Methylenemalononitriles and Enals for Access to Complex Tetrahydrocarbazoles

AU - Mou, Chengli

AU - Zhou, Liejin

AU - Song, Runjiang

AU - Chai, Huifang

AU - Hao, Lin

AU - Chi, Yonggui Robin

PY - 2020/4/3

Y1 - 2020/4/3

N2 - A carbene-catalyzed enantioselective cascade reaction of substituted methylenemalononitriles and α-bromoenals is disclosed. Key steps of this cascade process include a formal [4 + 2] cycloaddition, aldol reaction, and intramolecular lactonization. Our reaction offers streamlined and highly stereoselective access to complex tetrahydrocarbazole derivatives, with simultaneous formation of four chemical bonds and four chiral centers.

AB - A carbene-catalyzed enantioselective cascade reaction of substituted methylenemalononitriles and α-bromoenals is disclosed. Key steps of this cascade process include a formal [4 + 2] cycloaddition, aldol reaction, and intramolecular lactonization. Our reaction offers streamlined and highly stereoselective access to complex tetrahydrocarbazole derivatives, with simultaneous formation of four chemical bonds and four chiral centers.

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EP - 2547

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

Carbene-Catalyzed Reaction of Indolyl Methylenemalononitriles and Enals for Access to Complex Tetrahydrocarbazoles

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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