Lanthanum aryloxide/pybox-catalyzed direct asymmetric mannich-type reactions using a trichloromethyl ketone as a propionate equivalent donor

Hiroyuki Morimoto, Gang Lu, Naohiro Aoyama, Shigeki Matsunaga, Masakatsu Shibasaki

Research output: Contribution to journalArticle

87 Citations (Scopus)

Abstract

Direct catalytic asymmetric Mannich-type reaction of a trichloromethyl ketone as a propionate equivalent donor is described. A new lanthanum aryloxide-iPr-pybox + lithium aryloxide combined catalyst was the most effective, promoting the reaction of N-2-thiophenesulfonyl imines with the trichloromethyl ketone. syn-Mannich adducts were obtained from various aryl, heteroaryl, alkenyl, and alkyl imines in > 99-72% yield, syn/anti of > 30:1-8:1, and 98-92% ee (from a propionate equivalent donor) using 2.5-10 mol % catalyst. The Mannich adduct was converted not only into ester but also into useful building blocks.

Original languageEnglish
Pages (from-to)9588-9589
Number of pages2
JournalJournal of the American Chemical Society
Volume129
Issue number31
DOIs
Publication statusPublished - Aug 8 2007
Externally publishedYes

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Lanthanum
Imines
Propionates
Ketones
Catalysts
Lithium
Esters

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Lanthanum aryloxide/pybox-catalyzed direct asymmetric mannich-type reactions using a trichloromethyl ketone as a propionate equivalent donor. / Morimoto, Hiroyuki; Lu, Gang; Aoyama, Naohiro; Matsunaga, Shigeki; Shibasaki, Masakatsu.

In: Journal of the American Chemical Society, Vol. 129, No. 31, 08.08.2007, p. 9588-9589.

Research output: Contribution to journalArticle

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AB - Direct catalytic asymmetric Mannich-type reaction of a trichloromethyl ketone as a propionate equivalent donor is described. A new lanthanum aryloxide-iPr-pybox + lithium aryloxide combined catalyst was the most effective, promoting the reaction of N-2-thiophenesulfonyl imines with the trichloromethyl ketone. syn-Mannich adducts were obtained from various aryl, heteroaryl, alkenyl, and alkyl imines in > 99-72% yield, syn/anti of > 30:1-8:1, and 98-92% ee (from a propionate equivalent donor) using 2.5-10 mol % catalyst. The Mannich adduct was converted not only into ester but also into useful building blocks.

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