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Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling.

ABSTRACT: The rhodium-catalyzed enantioselective desymmetrization of symmetric ?,?-unsaturated amides via carbonyl-directed catalytic asymmetric hydroboration (directed CAHB) affords chiral secondary organoboronates with up to 98% ee. The chiral ?-borylated products undergo palladium-catalyzed Suzuki-Miyaura cross-coupling via the trifluoroborate salt with stereoretention.

SUBMITTER: Hoang GL

PROVIDER: S-EPMC4385711 | biostudies-other | 2015 Feb

REPOSITORIES: biostudies-other

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Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling.

Hoang Gia L GL Yang Zhao-Di ZD Smith Sean M SM Pal Rhitankar R Miska Judy L JL Pérez Damaris E DE Pelter Libbie S W LS Zeng Xiao Cheng XC Takacs James M JM

Organic letters 20150202 4

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. ...[more]

PMID: 25642639

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