Carbene-catalyzed enantioselective addition of benzylic carbon to unsaturated acyl azolium for rapid synthesis of pyrrolo[3,2- c]quinolines

Carbene-catalyzed enantioselective addition of benzylic carbon to unsaturated acyl azolium for rapid synthesis of pyrrolo[3,2- c]quinolines

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[...

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Bibliographic Details
Main Authors: Wang, Jilan, Li, Yongjia, Sun, Jun, Wang, Hong, Jin, Zhichao, Chi, Robin Yonggui
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2020
Subjects:
Science::Chemistry::Organic chemistry
Carbene Organocatalysis
Asymmetric Synthesis
Online Access:https://hdl.handle.net/10356/138266
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Institution: Nanyang Technological University
Language: English
Description
Summary: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.

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