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Issue 45, 2013
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The development of highly active acyclic chiral hydrazides for asymmetric iminium ion organocatalysis

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Abstract

Double asymmetric induction has been employed as a tool to optimise pyrazolidinone-derived organocatalysts for the asymmetric iminium ion catalysed Diels–Alder reaction. Mechanistic studies revealed a superior hydrazide catalyst deriving from methanolysis of the chiral pyrazolidinone precursor. This catalyst displays unusually high endo diastereoselectivity and good enantioselectivity with a range of β-arylenals and cyclic dienes at catalyst loadings as low as 1 mol%.

Graphical abstract: The development of highly active acyclic chiral hydrazides for asymmetric iminium ion organocatalysis

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Publication details

The article was received on 22 Aug 2013, accepted on 27 Sep 2013 and first published on 16 Oct 2013


Article type: Paper
DOI: 10.1039/C3OB41719K
Citation: Org. Biomol. Chem., 2013,11, 7877-7892
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    The development of highly active acyclic chiral hydrazides for asymmetric iminium ion organocatalysis

    E. Gould, T. Lebl, A. M. Z. Slawin, M. Reid, T. Davies and A. D. Smith, Org. Biomol. Chem., 2013, 11, 7877
    DOI: 10.1039/C3OB41719K

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