Organoammonium salt-catalyzed enantioselective cycloaddition reactions with α-(Acyloxy)- or α-diacylaminoacroleins

Akira Sakakura, Kazuaki Ishihara

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12 Citations (Scopus)

Abstract

The rational design of small-molecule chiral catalysts is an important subject in the development of practical organic syntheses. We have designed primary ammonium salt catalysts for enantioselective cycloaddition reactions with α- substituted acroleins such as α-(acyloxy)acroleins and α-diacylaminoacroleins. Ammonium salts of an aliphatic triamine derived from HL-Phe-L-Leu-N(CH2CH2)2 successfully promote the DielsAlder reaction of α-(acyloxy)acroleins and α-(N,N-diacylamino)acroleins, and the [2 + 2] cycloaddition reaction of α-(acyloxy)acroleins with high enantioselectivity. An ammonium salt of a C2-symmetric aromatic diamine, 1,1′-binaphthyl-2,2′- diamine, with a superacid is also an efficient catalyst and shows high activity and enantioselectivity for the DielsAlder reaction of cyclic dienes with α-(acyloxy)acroleins.

Original languageEnglish
Pages (from-to)313-322
Number of pages10
JournalBulletin of the Chemical Society of Japan
Volume83
Issue number4
DOIs
Publication statusPublished - 2010
Externally publishedYes

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Cycloaddition
Ammonium Compounds
Diamines
Salts
Enantioselectivity
Catalysts
Molecules

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Organoammonium salt-catalyzed enantioselective cycloaddition reactions with α-(Acyloxy)- or α-diacylaminoacroleins",
abstract = "The rational design of small-molecule chiral catalysts is an important subject in the development of practical organic syntheses. We have designed primary ammonium salt catalysts for enantioselective cycloaddition reactions with α- substituted acroleins such as α-(acyloxy)acroleins and α-diacylaminoacroleins. Ammonium salts of an aliphatic triamine derived from HL-Phe-L-Leu-N(CH2CH2)2 successfully promote the DielsAlder reaction of α-(acyloxy)acroleins and α-(N,N-diacylamino)acroleins, and the [2 + 2] cycloaddition reaction of α-(acyloxy)acroleins with high enantioselectivity. An ammonium salt of a C2-symmetric aromatic diamine, 1,1′-binaphthyl-2,2′- diamine, with a superacid is also an efficient catalyst and shows high activity and enantioselectivity for the DielsAlder reaction of cyclic dienes with α-(acyloxy)acroleins.",
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T1 - Organoammonium salt-catalyzed enantioselective cycloaddition reactions with α-(Acyloxy)- or α-diacylaminoacroleins

AU - Sakakura, Akira

AU - Ishihara, Kazuaki

PY - 2010

Y1 - 2010

N2 - The rational design of small-molecule chiral catalysts is an important subject in the development of practical organic syntheses. We have designed primary ammonium salt catalysts for enantioselective cycloaddition reactions with α- substituted acroleins such as α-(acyloxy)acroleins and α-diacylaminoacroleins. Ammonium salts of an aliphatic triamine derived from HL-Phe-L-Leu-N(CH2CH2)2 successfully promote the DielsAlder reaction of α-(acyloxy)acroleins and α-(N,N-diacylamino)acroleins, and the [2 + 2] cycloaddition reaction of α-(acyloxy)acroleins with high enantioselectivity. An ammonium salt of a C2-symmetric aromatic diamine, 1,1′-binaphthyl-2,2′- diamine, with a superacid is also an efficient catalyst and shows high activity and enantioselectivity for the DielsAlder reaction of cyclic dienes with α-(acyloxy)acroleins.

AB - The rational design of small-molecule chiral catalysts is an important subject in the development of practical organic syntheses. We have designed primary ammonium salt catalysts for enantioselective cycloaddition reactions with α- substituted acroleins such as α-(acyloxy)acroleins and α-diacylaminoacroleins. Ammonium salts of an aliphatic triamine derived from HL-Phe-L-Leu-N(CH2CH2)2 successfully promote the DielsAlder reaction of α-(acyloxy)acroleins and α-(N,N-diacylamino)acroleins, and the [2 + 2] cycloaddition reaction of α-(acyloxy)acroleins with high enantioselectivity. An ammonium salt of a C2-symmetric aromatic diamine, 1,1′-binaphthyl-2,2′- diamine, with a superacid is also an efficient catalyst and shows high activity and enantioselectivity for the DielsAlder reaction of cyclic dienes with α-(acyloxy)acroleins.

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