Direct enolization chemistry of 7-azaindoline amides: A case study of bis(tetrahydrophosphole)-type ligands

Zhao Li, Hidetoshi Noda, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

7-Azaindoline amides are particularly useful in direct enolization chemistry due to their facilitated enolization in soft Lewis acid/Brønsted base cooperative catalysis. The Cu(I) complex of (R,R)-Ph-BPE, a bis(tetrahydrophosphole)-type chiral bisphosphine ligand, exhibits consistently high catalytic performance and stereoselectivity irrespective of the nature of the α-substituent of the amides. Unexpectedly, however, alkyl-substituted bis(tetrahydrophosphole)-type ligands have substantially inferior catalytic performance. Evaluation of the optimized structures of Cu(I)/amide and Cu(I)/enolate complexes provided clues to dissecting the diverted reaction outcomes.

Original languageEnglish
Pages (from-to)3301-3305
Number of pages5
JournalTetrahedron
Volume74
Issue number26
DOIs
Publication statusPublished - 2018 Jun 28
Externally publishedYes

Keywords

  • Aldol reaction
  • Asymmetric catalysis
  • Copper
  • Enolates
  • Mannich reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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