Enantioselective Desymmetrization via Carbonyl-Directed Catalytic Asymmetric Hydroboration and Suzuki–Miyaura Cross-Coupling

Enantioselective Desymmetrization via Carbonyl-Directed Catalytic Asymmetric Hydroboration and Suzuki–Miyaura Cross-Coupling

The rhodium-catalyzed enantioselective desymmetrization of symmetric γ,δ-unsaturated amides via carbonyl-directed catalytic asymmetric hydroboration (directed CAHB) affords chiral secondary organoboronates with up to 98% ee. The chiral γ-borylated products undergo palladium-catalyzed Suzuki–Miyaura...

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Bibliographic Details
Published in:Organic letters Vol. 17; no. 4; pp. 940 - 943
Main Authors: Hoang, Gia L, Yang, Zhao-Di, Smith, Sean M, Pal, Rhitankar, Miska, Judy L, Pérez, Damaris E, Pelter, Libbie S. W, Zeng, Xiao Cheng, Takacs, James M
Format: Journal Article
Language:English
Published: United States American Chemical Society 20-02-2015
Subjects:
Amides - chemistry
Boron Compounds - chemistry
Catalysis
Cross-Linking Reagents
Molecular Structure
Palladium - chemistry
Rhodium - chemistry
Stereoisomerism
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Summary:The rhodium-catalyzed enantioselective desymmetrization of symmetric γ,δ-unsaturated amides via carbonyl-directed catalytic asymmetric hydroboration (directed CAHB) affords chiral secondary organoboronates with up to 98% ee. The chiral γ-borylated products undergo palladium-catalyzed Suzuki–Miyaura cross-coupling via the trifluoroborate salt with stereoretention.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol503764d