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Enantio- and diastereoselective conjugate borylation/Mannich cyclization.

ABSTRACT: Strategies to capitalize on enolate intermediates generated from stereoselective conjugate borylation to α,β-unsaturated carbonyl systems are surprisingly rare despite the ubiquity of Michael acceptors, and the potential to generate valuable scaffolds bearing multiple stereocenters. Herein, we report a mild and stereoselective copper-catalyzed conjugate borylation/Mannich cyclization reaction. This strategy is feasible with a broad range of Michael acceptors, and can be leveraged to generate versatile borylated tetrahydroquinoline scaffolds bearing three contiguous stereocenters. The synthetic potential of these complex heterocycles has been explored through a series of derivatization studies.

SUBMITTER: Larin EM

PROVIDER: S-EPMC8159378 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Enantio- and diastereoselective conjugate borylation/Mannich cyclization.

Larin Egor M EM Loup Joachim J Polishchuk Iuliia I Ross Rachel J RJ Whyte Andrew A Lautens Mark M

Chemical science 20200518 22

Strategies to capitalize on enolate intermediates generated from stereoselective conjugate borylation to α,β-unsaturated carbonyl systems are surprisingly rare despite the ubiquity of Michael acceptors, and the potential to generate valuable scaffolds bearing multiple stereocenters. Herein, we report a mild and stereoselective copper-catalyzed conjugate borylation/Mannich cyclization reaction. This strategy is feasible with a broad range of Michael acceptors, and can be leveraged to generate ver ...[more]

PMID: 34094079

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