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Enantioselective Redox-Neutral Coupling of Aldehydes and Alkenes by an Iron-Catalyzed "Catch-Release" Tethering Approach.

ABSTRACT: The reductive coupling of aldehydes and alkenes is an emerging technology that holds the potential to reinvent carbonyl addition chemistry. However, existing enantioselective methods are limited to form "branched" products. Herein, we present a directed enantio- and diastereoselective alkylation of aldehydes with simple olefins to selectively yield linear coupling products. This is achieved by redox-neutral remote functionalization, whereby a tethering "catch-release" strategy decisively solves the key problems of reactivity and selectivity.

SUBMITTER: Li J

PROVIDER: S-EPMC6342409 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Enantioselective Redox-Neutral Coupling of Aldehydes and Alkenes by an Iron-Catalyzed "Catch-Release" Tethering Approach.

Li Jing J Preinfalk Alexander A Maulide Nuno N

Journal of the American Chemical Society 20181221 1

The reductive coupling of aldehydes and alkenes is an emerging technology that holds the potential to reinvent carbonyl addition chemistry. However, existing enantioselective methods are limited to form "branched" products. Herein, we present a directed enantio- and diastereoselective alkylation of aldehydes with simple olefins to selectively yield linear coupling products. This is achieved by redox-neutral remote functionalization, whereby a tethering "catch-release" strategy decisively solves ...[more]

PMID: 30576130

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