Enantioselective Photocatalytic [3 + 2] Cycloadditions of Aryl Cyclopropyl Ketones

Adrian G. Amador, Evan M. Sherbrook, Tehshik P. Yoon

Research output: Contribution to journalArticlepeer-review

133 Scopus citations

Abstract

Control of stereochemistry in photocycloaddition reactions remains a substantial challenge; almost all successful catalytic examples to date have involved [2 + 2] photocycloadditions of enones. We report a method for the asymmetric [3 + 2] photocycloaddition of aryl cyclopropyl ketones that enables the enantiocontrolled construction of densely substituted cyclopentane structures not synthetically accessible using other catalytic methods. These results show that the dual-catalyst strategy developed in our laboratory broadens synthetic chemists' access to classes of photochemical cycloadditions that have not previously been feasible in enantioselective form.

Original languageEnglish (US)
Pages (from-to)4722-4725
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number14
DOIs
StatePublished - Apr 27 2016

Bibliographical note

Funding Information:
We thank Ilia Guzei for determination of the absolute configuration of 11 by X-ray crystallographic analysis. We are grateful to the NIH (GM098886) for financial support and to Sigma-Aldrich for a generous gift of RuCl3. The NMR facilities at UW-Madison are supported by a generous gift from the Paul J. Bender fund.

Publisher Copyright:
© 2016 American Chemical Society.

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