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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Abstract

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:	24 Nov 2024 08:30
URI:	https://orca.cardiff.ac.uk/id/eprint/124107

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