Catalytic asymmetric amination of N-nonsubstituted α-alkoxycarbonyl amides: Concise enantioselective synthesis of mycestericina F and G

Farouk Berhal, Sho Takechi, Naoya Kumagai, Masakatsu Shibasaki

研究成果: Article査読

43 被引用数 (Scopus)

抄録

In an attempt to explore the synthetic utility of a ternary asymmetric catalyst comprising La(NO3)3·6H2O, amide-based ligand (R)-L1, and D-valine tert-butyl ester H-D-Val-OtBu, we investigated a catalytic, asymmetric amination of functionalized N-nonsubstituted α-alkoxycarbonyl amides using di-tert-butyl azodicarboxylate as an electrophilic aminating reagent. A highly functionalized, cyclic N-nonsubstituted α-alkoxycarbonyl amide delivered the desired amination product in up to 96% enantiometric excess, with the requisite functionalities of the polar heads of sphingosines with the appropriate stereochemical arrangement. The rapid asymmetric assembly of these functional groups allowed a concise enantioselective synthetic route to sphingosines to be established with a broad flexibility towards derivative synthesis. These studies have culminated in an efficient catalytic enantioselective total synthesis of immunosuppressive fungal metabolites mycestericina F (3a) and G (3b).

本文言語English
ページ(範囲)1915-1921
ページ数7
ジャーナルChemistry - A European Journal
17
6
DOI
出版ステータスPublished - 2011 12月 7
外部発表はい

ASJC Scopus subject areas

  • 触媒
  • 有機化学

フィンガープリント

「Catalytic asymmetric amination of N-nonsubstituted α-alkoxycarbonyl amides: Concise enantioselective synthesis of mycestericina F and G」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル