Catalytic Asymmetric Reactions with N,O-Aminals

Yi-Yong Huang, Chen Cai, Xing Yang, Zong-Chao Lv, Uwe Schneider

Research output: Contribution to journalLiterature reviewpeer-review

Abstract

N,O-aminals, molecules bearing a geminally N,O -substituted (stereogenic) carbon center, have been recently recognized as an important class of building blocks in organic synthesis. As direct precursors of imines and iminium ions, N,O-aminals were converted through asymmetric organocatalysis or metal catalysis to diverse enantiomerically enriched compounds including N-heterocycles. Furthermore, cyclic N,O-hemiaminals acted as acyclic amino aldehyde surrogates, which were transformed to enantioenriched products otherwise challenging to access. Finally, cyclic N,O-aminals were formed in situ as key intermediates in asymmetric catalysis. In this review, we introduce a wide array of catalytic asymmetric protocols involving the use of four distinct types of N,O-aminals as starting materials or key intermediates.

Original languageEnglish
Pages (from-to)5747-5763
Number of pages17
JournalACS Catalysis
Volume6
Issue number9
Early online date15 Jul 2016
DOIs
Publication statusE-pub ahead of print - 15 Jul 2016

Keywords

  • aminal
  • hemiaminal
  • carbinolamine
  • acetal
  • asymmetric catalysis
  • heterocycles
  • iminium ion
  • imine
  • CHIRAL PHOSPHORIC-ACID
  • N-ACYLIMINIUM IONS
  • FRIEDEL-CRAFTS REACTION
  • C-H ACTIVATION
  • PALLADIUM(II)-CATALYZED ENANTIOSELECTIVE SYNTHESIS
  • ORGANOCATALYTIC TRANSFER HYDROGENATION
  • TETRAHYDRO-BETA-CARBOLINES
  • BAYLIS-HILLMAN REACTION
  • MANNICH-TYPE REACTIONS
  • DIELS-ALDER REACTION

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