Organocatalytic Enantioselective 1,3-dipolar [6+4] Cycloadditions of Tropone

Chemistry : a European Journal
Giulio BertuzziKarl Anker Jørgensen

Abstract

A highly stereoselective 1,3-dipolar [6+4] cycloaddition towards bridged azobicyclo[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 dr and up to 99% ee. A series of transformations, as well as mechanistic proposals, are presented.

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Citations

May 13, 2021·Organic & Biomolecular Chemistry·Ziying ZhangQilin Wang
Jun 9, 2021·Angewandte Chemie·Nicolaj Inunnguaq JessenKarl Anker Jørgensen
Jan 9, 2021·Journal of the American Chemical Society·Xiangyang ChenK N Houk

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