Carbene-catalyzed activation of formyl-phenylacetic esters for access to chiral dihydroisoquinolinones

Carbene-catalyzed activation of formyl-phenylacetic esters for access to chiral dihydroisoquinolinones

A carbene-catalyzed reaction to synthesize chiral dihydroisoquinolinones via an o-quinodimethane (o-QDM) intermediate is disclosed. o-QDM reacts with cyclic sulfonic imines via annulation to afford highly enantioenriched dihydroisoquinolinone products. ESI-HRMS studies suggest a stepwise Mannich add...

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Bibliographic Details
Main Authors: Wu, Shuquan, Xu, Jun, Deng, Rui, Wang, Hongling, Chi, Robin Yonggui, Zheng, Pengcheng
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2022
Subjects:
Science::Chemistry
Substituents
Chemical Reactions
Online Access:https://hdl.handle.net/10356/155070
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Institution: Nanyang Technological University
Language: English
Description
Summary:A carbene-catalyzed reaction to synthesize chiral dihydroisoquinolinones via an o-quinodimethane (o-QDM) intermediate is disclosed. o-QDM reacts with cyclic sulfonic imines via annulation to afford highly enantioenriched dihydroisoquinolinone products. ESI-HRMS studies suggest a stepwise Mannich addition and acylation reaction pathway, and the pathways of the catalytic and uncatalyzed background reactions are evaluated via DFT calculations.

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