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

Gia L. Hoang; Zhao Di Yang; Sean M. Smith; Rhitankar Pal; Judy L. Miska; Damaris E. Pérez; Libbie S.W. Pelter; Xiao Cheng Zeng; James M. Takacs

doi:10.1021/ol503764d

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

Gia L. Hoang, Zhao Di Yang, Sean M. Smith, Rhitankar Pal, Judy L. Miska, Damaris E. Pérez, Libbie S.W. Pelter, Xiao Cheng Zeng, James M. Takacs

Chemistry

Research output: Contribution to journal › Article › peer-review

28 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	940-943
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	4
DOIs	https://doi.org/10.1021/ol503764d
State	Published - Feb 20 2015

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol503764d

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

In: Organic Letters, Vol. 17, No. 4, 20.02.2015, p. 940-943.

Research output: Contribution to journal › Article › peer-review

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abstract = "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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AU - Hoang, Gia L.

AU - Yang, Zhao Di

AU - Smith, Sean M.

AU - Pal, Rhitankar

AU - Miska, Judy L.

AU - Pérez, Damaris E.

AU - Pelter, Libbie S.W.

AU - Zeng, Xiao Cheng

AU - Takacs, James M.

PY - 2015/2/20

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N2 - 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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Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling

Abstract

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