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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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

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spelling	sg-ntu-dr.10356-1550702022-02-22T08:24:35Z Carbene-catalyzed activation of formyl-phenylacetic esters for access to chiral dihydroisoquinolinones Wu, Shuquan Xu, Jun Deng, Rui Wang, Hongling Chi, Robin Yonggui Zheng, Pengcheng School of Physical and Mathematical Sciences Science::Chemistry Substituents Chemical Reactions 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. Ministry of Education (MOE) Nanyang Technological University National Research Foundation (NRF) We acknowledge financial support from the National Natural Science Foundation of China (22061007, 21807019, 21772029, 21801051, 21961006, and 22071036); the 10 Talent Plan (Shicengci) of Guizhou Province ([2016]5649); the Guizhou Province Returned Oversea Student Science and Technology Activity Program ((2014)-2); the Science and Technology Department of Guizhou Province ([2018]2802 and [2019]1020); the Program of Introducing Talents of Discipline to Universities of China (111 Program, D20023) at Guizhou University; the Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules, Department of Education, Guizhou Province (Qianjiaohe KY (2020)004); the Guizhou Province FirstClass Disciplines Project ((Yiliu Xueke Jianshe Xiangmu)-GNYL(2017)008); Guizhou University of Traditional Chinese Medicine and Guizhou University (China); the Singapore National Research Foundation under its NRF Investigatorship (NRFNRFI2016-06) and Competitive Research Program (NRFCRP22-2019-0002); the Ministry of Education, Singapore, under its MOE AcRF Tier 1 Award (RG7/20 and RG5/19), its MOE AcRF Tier 2 Award (MOE2019-T2-2-117), and its MOE AcRF Tier 3 Award (MOE2018-T3-1-003); a Nanyang Research Award Grant; and a Chair Professorship Grant, Nanyang Technological University. 2022-02-22T08:24:35Z 2022-02-22T08:24:35Z 2021 Journal Article Wu, S., Xu, J., Deng, R., Wang, H., Chi, R. Y. & Zheng, P. (2021). Carbene-catalyzed activation of formyl-phenylacetic esters for access to chiral dihydroisoquinolinones. Organic Letters, 23(19), 7513-7517. https://dx.doi.org/10.1021/acs.orglett.1c02676 1523-7060 https://hdl.handle.net/10356/155070 10.1021/acs.orglett.1c02676 34533322 2-s2.0-85116005465 19 23 7513 7517 en NRFNRFI2016-06 NRFCRP22-2019-0002 RG7/20 RG5/19 MOE2019-T2-2-117 MOE2018-T3-1-003 Organic Letters © 2021 American Chemical Society. All rights reserved.
institution	Nanyang Technological University
building	NTU Library
continent	Asia
country	Singapore Singapore
content_provider	NTU Library
collection	DR-NTU
language	English
topic	Science::Chemistry Substituents Chemical Reactions
spellingShingle	Science::Chemistry Substituents Chemical Reactions Wu, Shuquan Xu, Jun Deng, Rui Wang, Hongling Chi, Robin Yonggui Zheng, Pengcheng Carbene-catalyzed activation of formyl-phenylacetic esters for access to chiral dihydroisoquinolinones
description	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.
author2	School of Physical and Mathematical Sciences
author_facet	School of Physical and Mathematical Sciences Wu, Shuquan Xu, Jun Deng, Rui Wang, Hongling Chi, Robin Yonggui Zheng, Pengcheng
format	Article
author	Wu, Shuquan Xu, Jun Deng, Rui Wang, Hongling Chi, Robin Yonggui Zheng, Pengcheng
author_sort	Wu, Shuquan
title	Carbene-catalyzed activation of formyl-phenylacetic esters for access to chiral dihydroisoquinolinones
title_short	Carbene-catalyzed activation of formyl-phenylacetic esters for access to chiral dihydroisoquinolinones
title_full	Carbene-catalyzed activation of formyl-phenylacetic esters for access to chiral dihydroisoquinolinones
title_fullStr	Carbene-catalyzed activation of formyl-phenylacetic esters for access to chiral dihydroisoquinolinones
title_full_unstemmed	Carbene-catalyzed activation of formyl-phenylacetic esters for access to chiral dihydroisoquinolinones
title_sort	carbene-catalyzed activation of formyl-phenylacetic esters for access to chiral dihydroisoquinolinones
publishDate	2022
url	https://hdl.handle.net/10356/155070
_version_	1725985783039393792

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

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