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Synthesis and Suzuki-Miyaura Cross-Coupling of Enantioenriched Secondary Potassium ?-Trifluoroboratoamides: Catalytic, Asymmetric Conjugate Addition of Bisboronic Acid and Tetrakis(dimethylamino)diboron to ?,?-Unsaturated Carbonyl Compounds.

ABSTRACT: Enantioenriched potassium ?-trifluoroboratoamides have been synthesized via an asymmetric, copper-catalyzed 1,4-addition of tetrahydroxydiboron (BBA) and tetrakis(dimethylamino)diboron to ?,?-unsaturated amides. These dibora reagents provide access to the desired organotrifluoroborates using effective and atom economical sources of boron. The copper-catalyzed ?-boration is extended to ?,?-unsaturated ketones and esters. Desired potassium organotrifluoroborates are synthesized with yields up to 92% and enantiomeric ratios up to 98:2. The enantioenriched potassium ?-trifluoroboratoamides are successfully cross-coupled with an array of aryl and heteroaryl chlorides in high yield with complete stereochemical fidelity as the transmetalation proceeds through an SE2 mechanism via an open transition state.

SUBMITTER: Molander GA 

PROVIDER: S-EPMC3984882 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

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Synthesis and Suzuki-Miyaura Cross-Coupling of Enantioenriched Secondary Potassium <i>β</i>-Trifluoroboratoamides: Catalytic, Asymmetric Conjugate Addition of Bisboronic Acid and Tetrakis(dimethylamino)diboron to <i>α</i>,<i>β</i>-Unsaturated Carbonyl Compounds.

Molander Gary A GA   Wisniewski Steven R SR   Hosseini-Sarvari Mona M  

Advanced synthesis & catalysis 20131001 14-15

Enantioenriched potassium <i>β</i>-trifluoroboratoamides have been synthesized <i>via</i> an asymmetric, copper-catalyzed 1,4-addition of tetrahydroxydiboron (BBA) and tetrakis(dimethylamino)diboron to <i>α</i>,<i>β</i>-unsaturated amides. These dibora reagents provide access to the desired organotrifluoroborates using effective and atom economical sources of boron. The copper-catalyzed <i>β</i>-boration is extended to <i>α</i>,<i>β</i>-unsaturated ketones and esters. Desired potassium organotri  ...[more]

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