Carbene-Catalyzed Activation of Formyl-phenylacetic Esters for Access to Chiral Dihydroisoquinolinones

Shuquan Wu; Jun Xu; Rui Deng; Hongling Wang; Yonggui Robin Chi; Pengcheng Zheng

doi:10.1021/acs.orglett.1c02676

Carbene-Catalyzed Activation of Formyl-phenylacetic Esters for Access to Chiral Dihydroisoquinolinones

Shuquan Wu, Jun Xu, Rui Deng, Hongling Wang, Yonggui Robin Chi, Pengcheng Zheng^*

^*Corresponding author for this work

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

9 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	7513-7517
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.1c02676
Publication status	Published - Oct 1 2021
Externally published	Yes

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Publisher Copyright:
© 2021 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "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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T1 - Carbene-Catalyzed Activation of Formyl-phenylacetic Esters for Access to Chiral Dihydroisoquinolinones

AU - Wu, Shuquan

AU - Xu, Jun

AU - Deng, Rui

AU - Wang, Hongling

AU - Chi, Yonggui Robin

AU - Zheng, Pengcheng

PY - 2021/10/1

Y1 - 2021/10/1

N2 - 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.

AB - 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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JO - Organic Letters

JF - Organic Letters

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Carbene-Catalyzed Activation of Formyl-phenylacetic Esters for Access to Chiral Dihydroisoquinolinones

Abstract

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