Chiral 1,1′-binaphthyl-2,2′-diammonium salt catalysts for the enantioselective Diels-Alder reaction with α-acyloxyacroleins

Akira Sakakura, Kenji Suzuki, Kazuhiko Nakano, Kazuaki Ishihara

Research output: Contribution to journalArticle

110 Citations (Scopus)

Abstract

A diammonium salt of chiral 1,1′-binaphthyl-2,2′-diamine and trifluoromethanesulfonimide (Tf2NH) shows excellent catalytic activity and enantioselectivity for the Diels-Alder reaction of α-acyloxyacroleins with cyclic dienes. For example, in the presence of 5 mol % of the ammonium catalyst, the Diels-Alder reaction of α- (cyclohexanecarbonyloxy)acrolein with cyclopentadiene proceeded in EtCN at -75 °C to give the adducts in 88% yield with 92% exo and 91% ee. This catalyst can be easily prepared in situ by mixing the commercially available chiral diamine and Tf2NH.

Original languageEnglish
Pages (from-to)2229-2232
Number of pages4
JournalOrganic Letters
Volume8
Issue number11
DOIs
Publication statusPublished - May 25 2006
Externally publishedYes

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Diels-Alder reactions
Diamines
Cycloaddition Reaction
diamines
Salts
salts
Acrolein
Cyclopentanes
catalysts
Catalysts
Enantioselectivity
dienes
Ammonium Compounds
adducts
catalytic activity
Catalyst activity

ASJC Scopus subject areas

  • Molecular Medicine

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Chiral 1,1′-binaphthyl-2,2′-diammonium salt catalysts for the enantioselective Diels-Alder reaction with α-acyloxyacroleins. / Sakakura, Akira; Suzuki, Kenji; Nakano, Kazuhiko; Ishihara, Kazuaki.

In: Organic Letters, Vol. 8, No. 11, 25.05.2006, p. 2229-2232.

Research output: Contribution to journalArticle

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abstract = "A diammonium salt of chiral 1,1′-binaphthyl-2,2′-diamine and trifluoromethanesulfonimide (Tf2NH) shows excellent catalytic activity and enantioselectivity for the Diels-Alder reaction of α-acyloxyacroleins with cyclic dienes. For example, in the presence of 5 mol {\%} of the ammonium catalyst, the Diels-Alder reaction of α- (cyclohexanecarbonyloxy)acrolein with cyclopentadiene proceeded in EtCN at -75 °C to give the adducts in 88{\%} yield with 92{\%} exo and 91{\%} ee. This catalyst can be easily prepared in situ by mixing the commercially available chiral diamine and Tf2NH.",
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