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Chiral Brønsted acid-controlled intermolecular asymmetric [2 + 2] photocycloadditions

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Title
Chiral Brønsted acid-controlled intermolecular asymmetric [2 + 2] photocycloadditions
Author(s)
Sherbrook, Evan M.; Genzink, Matthew J.; Bohyun Park; Guzei, Ilia A.; Mu-Hyun Baik; Yoon, Tehshik P.
Publication Date
2021-12-01
Journal
Nature Communications, v.12, no.1
Publisher
Nature Research
Abstract
© 2021, The Author(s).Control over the stereochemistry of excited-state photoreactions remains a significant challenge in organic synthesis. Recently, it has become recognized that the photophysical properties of simple organic substrates can be altered upon coordination to Lewis acid catalysts, and that these changes can be exploited in the design of highly enantioselective catalytic photoreactions. Chromophore activation strategies, wherein simple organic substrates are activated towards photoexcitation upon binding to a Lewis acid catalyst, rank among the most successful asymmetric photoreactions. Herein, we show that chiral Brønsted acids can also catalyze asymmetric excited-state photoreactions by chromophore activation. This principle is demonstrated in the context of a highly enantio- and diastereoselective [2+2] photocycloaddition catalyzed by a chiral phosphoramide organocatalyst. Notably, the cyclobutane products arising from this method feature a trans-cis stereochemistry that is complementary to other enantioselective catalytic [2+2] photocycloadditions reported to date.
URI
https://pr.ibs.re.kr/handle/8788114/10586
DOI
10.1038/s41467-021-25878-9
ISSN
2041-1723
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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