Asymmetric organocatalytic tandem cyclization/transfer hydrogenation: A synthetic strategy for enantioenriched nitrogen heterocycles

Feng Shi, Wei Tan, Hong Hao Zhang, Mei Li, Qin Ye, Guan Hua Ma, Shu Jiang Tu, Guigen Li

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

An asymmetric organocatalytic tandem reaction comprising cyclization/transfer hydrogenation has been established in a compatible and synergistic way, leading to the step-economical synthesis of enantioenriched tetrahydroquinoxalines and dihydroquinoxalinones from readily accessible materials in excellent enantioselectivity of up to >99% ee. This protocol of a one-operation tandem reaction combines the merits of both tandem reactions and asymmetric organocatalysis, providing an efficient strategy for concisely and enantioselectively synthesizing nitrogen heterocycles with biological relevance.

Original languageEnglish
Pages (from-to)3715-3726
Number of pages12
JournalAdvanced Synthesis and Catalysis
Volume355
Issue number18
DOIs
StatePublished - Dec 16 2013

Keywords

  • asymmetric catalysis
  • enantioselectivity
  • organic catalysis
  • tandem reaction
  • transfer hydrogenation

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