Carbene-Catalyzed Enantioselective Addition of Benzylic Carbon to Unsaturated Acyl Azolium for Rapid Synthesis of Pyrrolo[3,2- c]quinolines

Jilan Wang; Yongjia Li; Jun Sun; Hongling Wang; Zhichao Jin; Yonggui Robin Chi

doi:10.1021/acscatal.8b02651

Carbene-Catalyzed Enantioselective Addition of Benzylic Carbon to Unsaturated Acyl Azolium for Rapid Synthesis of Pyrrolo[3,2- c]quinolines

Jilan Wang, Yongjia Li, Jun Sun, Hongling Wang, Zhichao Jin^*, Yonggui Robin Chi

^*Corresponding author for this work

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

17 Citations (Scopus)

Abstract

A carbene-catalyzed enantioselective addition of benzylic carbon to α,β-unsaturated acyl azolium intermediate generated via N-heterocyclic carbene catalysis is disclosed. This addition is followed by a stereoselective Mannich reaction and a chemo-selective lactam formation cascade to afford pyrrolo[3,2-c]quinolones as the products with excellent yields and optical purities. This work constitutes an effective asymmetric benzyl sp³-carbon functionalization and single-step rapid access to multicyclic heterocycles bearing four contiguous chiral centers.

Original language	English
Pages (from-to)	9859-9864
Number of pages	6
Journal	ACS Catalysis
Volume	8
Issue number	10
DOIs	https://doi.org/10.1021/acscatal.8b02651
Publication status	Published - Oct 5 2018
Externally published	Yes

Bibliographical note

Publisher Copyright:
Copyright © 2018 American Chemical Society.

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

asymmetric synthesis
benzylic carbon reaction
carbene organocatalysis
four contiguous chiral centers
pyrrolo[3,2- c]quinoline
α,β-unsaturated acylazolium

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10.1021/acscatal.8b02651

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title = "Carbene-Catalyzed Enantioselective Addition of Benzylic Carbon to Unsaturated Acyl Azolium for Rapid Synthesis of Pyrrolo[3,2- c]quinolines",

abstract = "A carbene-catalyzed enantioselective addition of benzylic carbon to α,β-unsaturated acyl azolium intermediate generated via N-heterocyclic carbene catalysis is disclosed. This addition is followed by a stereoselective Mannich reaction and a chemo-selective lactam formation cascade to afford pyrrolo[3,2-c]quinolones as the products with excellent yields and optical purities. This work constitutes an effective asymmetric benzyl sp3-carbon functionalization and single-step rapid access to multicyclic heterocycles bearing four contiguous chiral centers.",

keywords = "asymmetric synthesis, benzylic carbon reaction, carbene organocatalysis, four contiguous chiral centers, pyrrolo[3,2- c]quinoline, α,β-unsaturated acylazolium",

author = "Jilan Wang and Yongjia Li and Jun Sun and Hongling Wang and Zhichao Jin and Chi, \{Yonggui Robin\}",

note = "Publisher Copyright: Copyright {\textcopyright} 2018 American Chemical Society.",

year = "2018",

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day = "5",

doi = "10.1021/acscatal.8b02651",

language = "English",

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journal = "ACS Catalysis",

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T1 - Carbene-Catalyzed Enantioselective Addition of Benzylic Carbon to Unsaturated Acyl Azolium for Rapid Synthesis of Pyrrolo[3,2- c]quinolines

AU - Wang, Jilan

AU - Li, Yongjia

AU - Sun, Jun

AU - Wang, Hongling

AU - Jin, Zhichao

AU - Chi, Yonggui Robin

PY - 2018/10/5

Y1 - 2018/10/5

N2 - A carbene-catalyzed enantioselective addition of benzylic carbon to α,β-unsaturated acyl azolium intermediate generated via N-heterocyclic carbene catalysis is disclosed. This addition is followed by a stereoselective Mannich reaction and a chemo-selective lactam formation cascade to afford pyrrolo[3,2-c]quinolones as the products with excellent yields and optical purities. This work constitutes an effective asymmetric benzyl sp3-carbon functionalization and single-step rapid access to multicyclic heterocycles bearing four contiguous chiral centers.

AB - A carbene-catalyzed enantioselective addition of benzylic carbon to α,β-unsaturated acyl azolium intermediate generated via N-heterocyclic carbene catalysis is disclosed. This addition is followed by a stereoselective Mannich reaction and a chemo-selective lactam formation cascade to afford pyrrolo[3,2-c]quinolones as the products with excellent yields and optical purities. This work constitutes an effective asymmetric benzyl sp3-carbon functionalization and single-step rapid access to multicyclic heterocycles bearing four contiguous chiral centers.

KW - asymmetric synthesis

KW - benzylic carbon reaction

KW - carbene organocatalysis

KW - four contiguous chiral centers

KW - pyrrolo[3,2- c]quinoline

KW - α,β-unsaturated acylazolium

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DO - 10.1021/acscatal.8b02651

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VL - 8

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JO - ACS Catalysis

JF - ACS Catalysis

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Carbene-Catalyzed Enantioselective Addition of Benzylic Carbon to Unsaturated Acyl Azolium for Rapid Synthesis of Pyrrolo[3,2- c]quinolines

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

Access to Document

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