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Streamlined synthesis of C(sp3)-Rich N-Heterospirocycles enabled by visible-light-mediated photocatalysis

Flodén, Nils J., Trowbridge, Aaron, Willcox, Darren, Walton, Scarlett M., Kim, Yongjoon and Gaunt, Matthew J. 2019. Streamlined synthesis of C(sp3)-Rich N-Heterospirocycles enabled by visible-light-mediated photocatalysis. Journal of the American Chemical Society 141 (21) , pp. 8426-8430. 10.1021/jacs.9b03372

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We report a general visible-light-mediated strategy that enables the construction of complex C(sp3)-rich N-heterospirocycles from feedstock aliphatic ketones and aldehydes with a broad selection of alkene-containing secondary amines. Key to the success of this approach was the utilization of a highly reducing Ir-photocatalyst and orchestration of the intrinsic reactivities of 1,4-cyclohexadiene and Hantzsch ester. This methodology provides streamlined access to complex C(sp3)-rich N-heterospirocycles displaying structural and functional features relevant to fragment-based lead identification programs.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: American Chemical Society
ISSN: 0002-7863
Funders: EPSRC
Date of First Compliant Deposit: 10 July 2019
Date of Acceptance: 9 May 2019
Last Modified: 10 May 2020 16:38

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