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

Research output: Contribution to journalArticle

24 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)940-943
Number of pages4
JournalOrganic Letters
Volume17
Issue number4
DOIs
StatePublished - Feb 20 2015

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hydroboration
Rhodium
cross coupling
Palladium
rhodium
Amides
amides
palladium
Salts
salts
products

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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 journalArticle

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. / Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling. In: Organic Letters. 2015 ; Vol. 17, No. 4. pp. 940-943.
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AU - Pérez, Damaris E.

AU - Pelter, Libbie S.W.

AU - Zeng, Xiao Cheng

AU - Takacs, James M.

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