Organoammonium Salt-Catalyzed Enantioselective Cycloaddition Reactions with α-(Acyloxy)- or α-Diacylaminoacroleins

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-diacylaminoa...

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Published inBulletin of the Chemical Society of Japan Vol. 83; no. 4; pp. 313 - 322
Main Authors Sakakura, Akira, Ishihara, Kazuaki
Format Journal Article
LanguageEnglish
Published The Chemical Society of Japan 15.04.2010
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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 H–L-Phe–L-Leu–N(CH2CH2)2 successfully promote the Diels–Alder 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 Diels–Alder reaction of cyclic dienes with α-(acyloxy)acroleins.
AbstractList 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 H–L-Phe–L-Leu–N(CH2CH2)2 successfully promote the Diels–Alder 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 Diels–Alder reaction of cyclic dienes with α-(acyloxy)acroleins.
Author Ishihara, Kazuaki
Sakakura, Akira
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  surname: Ishihara
  fullname: Ishihara, Kazuaki
  organization: 2 Graduate School of Engineering, Nagoya University
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Snippet The rational design of small-molecule chiral catalysts is an important subject in the development of practical organic syntheses. We have designed primary...
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Title Organoammonium Salt-Catalyzed Enantioselective Cycloaddition Reactions with α-(Acyloxy)- or α-Diacylaminoacroleins
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