One-Pot Reductive Allylation of Amides by Using a Combination of Titanium Hydride and an Allylzinc Reagent: Application to a Total Synthesis of (-)-Castoramine

Suguru Itabashi, Masashi Shimomura, Manabu Sato, Hiroki Azuma, Kentaro Okano, Juri Sakata, Hidetoshi Tokuyama

研究成果: Article

8 引用 (Scopus)

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A one-pot direct reductive allylation protocol has been developed for the synthesis of secondary amines by using titanium hydride and an allylzinc reagent. This protocol is applicable to a broad range of substrates, including acyclic amides, benzamides, α,β-unsaturated amides, and lactams. The stereochemical outcome obtained from the reaction with crotylzinc reagent suggested that the allylation reaction proceeds through a six-membered cyclic transition state. A total synthesis of (-)-castoramine was accomplished by following this protocol for the highly stereoselective construction of contiguous stereocenters.

元の言語English
ページ(範囲)1786-1790
ページ数5
ジャーナルSynlett
29
発行部数13
DOI
出版物ステータスPublished - 2018 6 26

ASJC Scopus subject areas

  • Organic Chemistry

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