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

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1786-1790
Number of pages5
JournalSynlett
Volume29
Issue number13
DOIs
Publication statusPublished - 2018 Jun 26

Keywords

  • alkaloids
  • allylation
  • amides
  • amines
  • reduction
  • total synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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