Construction of Vicinal Quaternary Stereogenic Centers by Enantioselective Direct Mannich-Type Reaction Using a Chiral Bis(guanidino)iminophosphorane Catalyst

Tadahiro Takeda, Azusa Kondoh, Masahiro Terada

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

A novel asymmetric direct Mannich-type reaction of α-iminophenylacetate esters with thionolactones, bearing a substituent at the α-position, as a less acidic pronucleophile was developed. Using bis(guanidino)iminophosphorane as the chiral organosuperbase catalyst, the reaction afforded densely functionalized amino-acid derivatives having vicinal quaternary stereogenic centers, one of which is an all-carbon quaternary stereogenic center, in good yield with high diastereo- and enantioselectivities.

Original languageEnglish
Pages (from-to)4734-4737
Number of pages4
JournalAngewandte Chemie - International Edition
Volume55
Issue number15
DOIs
Publication statusPublished - 2016 Apr 4

Keywords

  • acidity
  • asymmetric catalysis
  • heterocycles
  • organocatalysis
  • phosphazene

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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