Chiral γ-amino amide synthesis by heterobimetallic lanthanum/lithium/pybox-catalyzed direct asymmetric Mannich-type reactions of α-keto anilides

Gang Lu, Hiroyuki Morimoto, Shigeki Matsunaga, Masakatsu Shibasaki

Research output: Contribution to journalArticle

55 Citations (Scopus)

Abstract

(Chemical Equation Presented) Not so Mannich now: A heterobimetallic La/Li/pybox complex was key in direct catalytic asymmetric Mannich-type reactions, using α-keto anilides as synthetic homoenolate equivalents to afford γ-amino amide products in up to > 99% yield, 95% ee, and >97:3 syn-selectivity. Stereoselective reduction of the α-keto moiety afforded the β-alkyl-γ-amino-α-hydroxy amide with three contiguous stereocenters (PG=protecting group).

Original languageEnglish
Pages (from-to)6847-6850
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number36
DOIs
Publication statusPublished - Aug 25 2008
Externally publishedYes

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Anilides
Lanthanum
Lithium
Amides

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Chiral γ-amino amide synthesis by heterobimetallic lanthanum/lithium/pybox-catalyzed direct asymmetric Mannich-type reactions of α-keto anilides. / Lu, Gang; Morimoto, Hiroyuki; Matsunaga, Shigeki; Shibasaki, Masakatsu.

In: Angewandte Chemie - International Edition, Vol. 47, No. 36, 25.08.2008, p. 6847-6850.

Research output: Contribution to journalArticle

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