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Asymmetric Synthesis of ß2 -Aryl Amino Acids through Pd-Catalyzed Enantiospecific and Regioselective Ring-Opening Suzuki-Miyaura Arylation of Aziridine-2-carboxylates.
Takeda, Youhei; Matsuno, Tetsuya; Sharma, Akhilesh K; Sameera, W M C; Minakata, Satoshi.
Afiliação
  • Takeda Y; Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka, 565-0871, Japan.
  • Matsuno T; Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka, 565-0871, Japan.
  • Sharma AK; Fukui Institute for Fundamental Chemistry, Kyoto University, Takano-Nishishiraki-cho 34-4, Sakyo-ku, Kyoto, 606-8103, Japan.
  • Sameera WMC; Institute of Low Temperature Science, Hokkaido University, Kita-ku, North 19 West 8, Sapporo, Hokkaido, 060-0819, Japan.
  • Minakata S; Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka, 565-0871, Japan.
Chemistry ; 25(43): 10226-10231, 2019 Aug 01.
Article em En | MEDLINE | ID: mdl-31161639
ABSTRACT
A Pd-catalyzed enantiospecific and regioselective ring-opening Suzuki-Miyaura arylation of aziridine-2-carboxylates was developed. The cross-coupling allows for the asymmetric preparation of enantioenriched ß2 -aryl amino acids, starting from commercially available enantiopure d- and l-serine esters. The mechanism and selectivity of the reaction was rationalized based on computational models.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Paládio / Aziridinas / Aminoácidos Idioma: En Ano de publicação: 2019 Tipo de documento: Article
Texto completo
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Paládio / Aziridinas / Aminoácidos Idioma: En Ano de publicação: 2019 Tipo de documento: Article