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Streamlined Synthesis of C(sp³)-Rich N-Heterospirocycles Enabled by Visible-Light-Mediated Photocatalysis

Author:
Flodén, Nils J., Trowbridge, Aaron, Willcox, Darren, Walton, Scarlett M., Kim, Yongjoon, Gaunt, Matthew J.
Source:
Journal of the American Chemical Society 2019 v.141 no.21 pp. 8426-8430
ISSN:
1520-5126
Subject:
aldehydes, feedstocks, ketones, lead, photocatalysis, secondary amines
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.
Agid:
6457098