A new type of amino amide organocatalyzed enantioselective crossed aldol reaction of ketones with aromatic aldehydes

Isiaka A. Owolabi, U. V. Subba Reddy, Madhu Chennapuram, Chigusa Seki, Yuko Okuyama, Eunsang Kwon, Koji Uwai, Michio Tokiwa, Mitsuhiro Takeshita, Hiroto Nakano

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

A new type of amino amide organocatalysts was designed and synthesized from commercially available amino acids in easy steps. Their catalytic activities were examined in enantioselective crossed aldol reaction of various acyclic and cyclic ketones with aromatic aldehydes to afford the corresponding chiral anti-aldol adducts with good to excellent chemical yields, diastereoselectivities and enantioselectivities (up to 99%, up to syn:anti = 1:99, up to 97% ee).

Original languageEnglish
Pages (from-to)4705-4711
Number of pages7
JournalTetrahedron
Volume74
Issue number36
DOIs
Publication statusPublished - 2018 Sep 6

Keywords

  • Aldehydes
  • Amino amide
  • Crossed aldol reaction
  • Ketones
  • Organocatalysis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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