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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
Published on: August 12, 2019
Organocatalytic Enantioselective 1,3-Dipolar [6+4] Cycloadditions of Tropone
Giulio Bertuzzi1, David McLeod1, Lisa-Marie Mohr1
1Department of Chemistry, Aarhus University, Langelandsgade 140, 8000, Aarhus C, Denmark.
Abstract:
A highly stereoselective 1,3-dipolar [6+4] cycloaddition towards bridged azabicyclo[4.3.1]decane scaffolds has been developed, reacting aldehydes, 2-aminomalonates and tropone under mild conditions in the presence of a chiral phosphoric acid catalyst. The scope is demonstrated for a series of aldehydes and 2-aminomalonates, and the reaction proceeds in high yields, >95:5 d.r. and up to 99 % ee. A series of transformations, as well as a mechanistic proposal, are presented.
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