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Expeditious diastereoselective synthesis of elaborated ketones via remote Csp3-H functionalization.


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.

SUBMITTER: Shu W 

PROVIDER: S-EPMC5241786 | biostudies-other | 2017 Jan

REPOSITORIES: biostudies-other

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Expeditious diastereoselective synthesis of elaborated ketones via remote Csp<sup>3</sup>-H functionalization.

Shu Wei W   Lorente Adriana A   Gómez-Bengoa Enrique E   Nevado Cristina C  

Nature communications 20170113


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 Csp<sup>3</sup>-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  ...[more]

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