Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
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Organoammonium Salt-Catalyzed Enantioselective Cycloaddition Reactions with α-(Acyloxy)- or α-Diacylaminoacroleins
Akira SakakuraKazuaki Ishihara
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2010 Volume 83 Issue 4 Pages 313-322

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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.

This account describes rational design of primary ammonium salt catalysts for enantioselective cycloaddition reactions with α-(acyloxy)acroleins and α-diacylaminoacroleins. The flexible asymmetric environment created using the chiral primary ammonium salts would be essential for the high-level induction of the enantioselectivity. Fullsize Image
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© 2010 The Chemical Society of Japan
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