Cooperative Stereoinduction in Asymmetric Photocatalysis

Chapman, Steven J.; Swords, Wesley B.; Le, Christine M.; Guzei, Ilia A.; Toste, F. Dean; Yoon, Tehshik P.

doi:10.1021/jacs.2c00063

Title: Cooperative Stereoinduction in Asymmetric Photocatalysis

Journal Article · 22 February 2022 · Journal of the American Chemical Society

DOI: https://doi.org/10.1021/jacs.2c00063 · OSTI ID:1987502

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University of Wisconsin−Madison, WI (United States)
University of California, Berkeley, CA (United States); York University, Ontario (Canada)
University of California, Berkeley, CA (United States)

Stereoinduction in complex organic reactions often involves the influence of multiple stereocontrol elements. The interaction among these can often result in the observation of significant cooperative effects that afford different rates and selectivities between the matched and mismatched sets of stereodifferentiating chiral elements. The elucidation of matched/mismatched effects in ground-state chemical reactions was a critically important theme in the maturation of modern stereocontrolled synthesis. The development of robust methods for the control of photochemical reactions, however, is a relatively recent development, and similar cooperative stereocontrolling effects in excited-state enantioselective photoreactions have not previously been documented. Herein, we describe a tandem chiral photocatalyst/Brønsted acid strategy for highly enantioselective [2 + 2] photocycloadditions of vinylpyridines. Importantly, the matched and mismatched chiral catalyst pairs exhibit different reaction rates and enantioselectivities across a range of coupling partners. We observe no evidence of ground-state interactions between the catalysts and conclude that these effects arise from their cooperative behavior in a transient excited-state assembly. Furthermore, these results suggest that similar matched/mismatched effects might be important in other classes of enantioselective dual-catalytic photochemical reactions.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: National Institute of Health (NIH); USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division (CSGB)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1987502

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 9 Vol. 144; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Catalysts
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CCDC 2130038: Experimental Crystal Structure Determination J., Chapman, Steven; B., Swords, Wesley; M., Le, Christine https://doi.org/10.5517/ccdc.csd.cc29hgx6 The current record is supplemented by this dataset	dataset	January 2022
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Title: Cooperative Stereoinduction in Asymmetric Photocatalysis

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References (35)

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