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

Advanced synthesis & catalysis, 2013-10, Vol.355 (14-15), p.3037-3057 [Peer Reviewed Journal]

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Title:
Synthesis and Suzuki-Miyaura Cross-Coupling of Enantioenriched Secondary Potassium [beta]-Trifluoroboratoamides: Catalytic, Asymmetric Conjugate Addition of Bisboronic Acid and Tetrakis(dimethylamino)diboron to [alpha],[beta]-Unsaturated Carbonyl Compounds
Author: Molander, Gary A ; Wisniewski, Steven R ; Hosseini-Sarvari, Mona
Subjects: Arrays
Is Part Of: Advanced synthesis & catalysis, 2013-10, Vol.355 (14-15), p.3037-3057
Description: Enantioenriched potassium [beta]-trifluoroboratoamides have been synthesized via an asymmetric, copper-catalyzed 1,4-addition of tetrahydroxydiboron (BBA) and tetrakis(dimethylamino)diboron to [alpha],[beta]-unsaturated amides. These dibora reagents provide access to the desired organotrifluoroborates using effective and atom economical sources of boron. The copper-catalyzed [beta]-boration is extended to [alpha],[beta]-unsaturated ketones and esters. The desired potassium organotrifluoroborates are synthesized with yields up to 92% and enantiomeric ratios up to 98:2. The enantioenriched potassium [beta]-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 S sub(E)2 mechanism via an open transition state.
Language: English
Identifier: ISSN: 1615-4150
EISSN: 1615-4169
DOI: 10.1002/adsc.201300640
Source: Alma/SFX Local Collection

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