Enantioselective sp3 C-H alkylation of γ-butyrolactam by a chiral Ir(i) catalyst for the synthesis of 4-substituted γ-amino acids

Yu Ki Tahara; Masamichi Michino; Mamoru Ito; Kyalo Stephen Kanyiva; Takanori Shibata

doi:10.1039/c5cc07102j

Enantioselective sp³ C-H alkylation of γ-butyrolactam by a chiral Ir(i) catalyst for the synthesis of 4-substituted γ-amino acids

Yu Ki Tahara, Masamichi Michino, Mamoru Ito, Kyalo Stephen Kanyiva, Takanori Shibata^*

^*Corresponding author for this work

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

64 Citations (Scopus)

Abstract

Ir-catalyzed sp³ C-H alkylation of γ-butyrolactam with alkenes was used for the highly enantioselective synthesis of 5-substituted γ-lactams, which were readily converted into chiral 4-substituted γ-amino acids. A broad scope of alkenes was amenable as coupling partners, and the alkylated product using acrylate could be transformed into the key intermediate of pyrrolam A synthesis.

Original language	English
Pages (from-to)	16660-16663
Number of pages	4
Journal	Chemical Communications
Volume	51
Issue number	93
DOIs	https://doi.org/10.1039/c5cc07102j
Publication status	Published - 2015

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
General Chemistry
Ceramics and Composites
Metals and Alloys
Materials Chemistry
Surfaces, Coatings and Films
Catalysis

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abstract = "Ir-catalyzed sp3 C-H alkylation of γ-butyrolactam with alkenes was used for the highly enantioselective synthesis of 5-substituted γ-lactams, which were readily converted into chiral 4-substituted γ-amino acids. A broad scope of alkenes was amenable as coupling partners, and the alkylated product using acrylate could be transformed into the key intermediate of pyrrolam A synthesis.",

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AU - Tahara, Yu Ki

AU - Michino, Masamichi

AU - Ito, Mamoru

AU - Kanyiva, Kyalo Stephen

AU - Shibata, Takanori

N1 - Publisher Copyright: © The Royal Society of Chemistry 2015.

PY - 2015

Y1 - 2015

N2 - Ir-catalyzed sp3 C-H alkylation of γ-butyrolactam with alkenes was used for the highly enantioselective synthesis of 5-substituted γ-lactams, which were readily converted into chiral 4-substituted γ-amino acids. A broad scope of alkenes was amenable as coupling partners, and the alkylated product using acrylate could be transformed into the key intermediate of pyrrolam A synthesis.

AB - Ir-catalyzed sp3 C-H alkylation of γ-butyrolactam with alkenes was used for the highly enantioselective synthesis of 5-substituted γ-lactams, which were readily converted into chiral 4-substituted γ-amino acids. A broad scope of alkenes was amenable as coupling partners, and the alkylated product using acrylate could be transformed into the key intermediate of pyrrolam A synthesis.

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Enantioselective sp³ C-H alkylation of γ-butyrolactam by a chiral Ir(i) catalyst for the synthesis of 4-substituted γ-amino acids

Abstract

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