Expeditious diastereoselective synthesis of elaborated ketones via remote Csp3–H functionalization

Wei Shu, Adriana Lorente, Enrique Gómez-Bengoa and Cristina Nevado ()
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Wei Shu: University of Zürich
Adriana Lorente: University of Zürich
Enrique Gómez-Bengoa: Universidad del Pais Vasco
Cristina Nevado: University of Zürich

Nature Communications, 2017, vol. 8, issue 1, 1-8

Abstract: Abstract The quest for selective C–H functionalization reactions, able to provide new strategic opportunities for the rapid assembly of molecular complexity, represents a major focus of the chemical community. Examples of non-directed, remote Csp3–H activation to forge complex carbon frameworks remain scarce due to the kinetic stability and thus intrinsic challenge associated to the chemo-, regio- and stereoselective functionalization of aliphatic C–H bonds. Here we describe a radical-mediated, directing-group-free regioselective 1,5-hydrogen transfer of unactivated Csp3–H bonds followed by a second Csp2–H functionalization to produce, with exquisite stereoselectivity, a variety of elaborated fused ketones. This study demonstrates that aliphatic acids can be strategically harnessed as 1,2-diradical synthons and that secondary aliphatic C–H bonds can be engaged in stereoselective C–C bond-forming reactions, highlighting the potential of this protocol for target-oriented natural product and pharmaceutical synthesis.

Date: 2017
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Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:8:y:2017:i:1:d:10.1038_ncomms13832

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DOI: 10.1038/ncomms13832

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