Catalytic asymmetric Michael reactions of dibenzyl malonate to α,β-unsaturated N-acylpyrroles using a La(O-iPr)3/Ph-linked-BINOL complex

So Young Park, Hiroyuki Morimoto, Shigeki Matsunaga, Masakatsu Shibasaki

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

Catalytic asymmetric Michael reactions of a malonate to acyclic α,β-unsaturated N-acylpyrroles as ester equivalent acceptors are described. A La(O-iPr)3/(S,S)-linked-BINOL complex, which is suitable for Michael addition to cyclic enones, is not suitable for acyclic α,β-unsaturated N-acylpyrroles. A new (S,S)-Ph-linked-BINOL chiral ligand was developed to improve enantioselectivity, and a La(O-iPr)3/(S,S)-Ph-linked-BINOL complex with the addition of HFIP afforded Michael adducts in good yield and enantioselectivity (up to 96% ee).

Original languageEnglish
Pages (from-to)2815-2818
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number16
DOIs
Publication statusPublished - Apr 16 2007
Externally publishedYes

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Enantioselectivity
Esters
Ligands
naphthol BINOL
malonic acid

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Catalytic asymmetric Michael reactions of dibenzyl malonate to α,β-unsaturated N-acylpyrroles using a La(O-iPr)3/Ph-linked-BINOL complex. / Park, So Young; Morimoto, Hiroyuki; Matsunaga, Shigeki; Shibasaki, Masakatsu.

In: Tetrahedron Letters, Vol. 48, No. 16, 16.04.2007, p. 2815-2818.

Research output: Contribution to journalArticle

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AU - Matsunaga, Shigeki

AU - Shibasaki, Masakatsu

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