Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/161331
Title: Carbene-catalyzed enantioselective sulfonylation of enone aryl aldehydes: a new mode of breslow intermediate oxidation
Authors: Deng, Rui
Wu, Shuquan
Mou, Chengli
Liu, Jianjian
Zheng, Pengcheng
Zhang, Xinglong
Chi, Robin Yonggui
Keywords: Science::Chemistry
Issue Date: 2022
Source: Deng, R., Wu, S., Mou, C., Liu, J., Zheng, P., Zhang, X. & Chi, R. Y. (2022). Carbene-catalyzed enantioselective sulfonylation of enone aryl aldehydes: a new mode of breslow intermediate oxidation. Journal of the American Chemical Society, 144(12), 5441-5449. https://dx.doi.org/10.1021/jacs.1c13384
Project: NRF-NRFI2016-06 
NRF-CRP22-2019-0002 
RG7/20 
RG5/19 
MOE2019-T2-2-117 
MOE2018-T3-1-003 
C210812008 
Journal: Journal of the American Chemical Society 
Abstract: A carbene-catalyzed sulfonylation reaction between enone aryl aldehydes and sulfonyl chlorides is disclosed. The reaction effectively installs sulfone moieties in a highly enantioselective manner to afford sulfone-containing bicyclic lactones. The sulfonyl chloride behaves both as an oxidant and a nucleophilic substrate (via its reduced form) in this N-heterocyclic carbene (NHC)-catalyzed process. The NHC catalyst provides both activation and stereoselectivity control on a very remote site of enone aryl aldehyde substrates. Water plays an important role in modulating catalyst deactivation and reactivation routes that involve reactions between NHC and sulfonyl chloride. Experimental studies and DFT calculations suggest that an unprecedented intermediate and a new oxidation mode of the NHC-derived Breslow intermediate are involved in the new asymmetric sulfonylation reaction.
URI: https://hdl.handle.net/10356/161331
ISSN: 0002-7863
DOI: 10.1021/jacs.1c13384
Schools: School of Physical and Mathematical Sciences 
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/jacs.1c13384.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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