Syntheses of arabinose-derived pyrrolidine catalysts and their applications in intramolecular Diels-Alder reactions

Tony K.M. Shing, Kwun W. Wu, Ho T. Wu, Qicai Xiao

研究成果: Article査読

4 被引用数 (Scopus)

抄録

Six chiral hydroxylated pyrrolidine catalysts were synthesized from commercially available D-arabinose in seven steps. Various aromatic substituents α to the amine can be introduced readily by a Grignard reaction, which enables facile optimization of the catalyst performance. The stereoselectivities of these catalysts have been assessed by comparing with those of MacMillan's imidazolidinone in a known intramolecular Diels-Alder (IMDA) reaction of a triene. Two additional IMDA reactions of symmetrical dienals with concomitant desymmetrisation further established the potential use of these novel amine catalysts. These pyrrolidines are valuable catalysts for other synthetic transformations.

本文言語English
ページ(範囲)1754-1762
ページ数9
ジャーナルOrganic and Biomolecular Chemistry
13
6
DOI
出版ステータスPublished - 2015 2月 14
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 物理化学および理論化学
  • 有機化学

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