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.

Bertuzzi G., McLeod D., Mohr L.-M., Jorgensen K.A. (2020). Organocatalytic Enantioselective 1,3-Dipolar [6+4] Cycloadditions of Tropone. CHEMISTRY-A EUROPEAN JOURNAL, 26(67), 15491-15496 [10.1002/chem.202003329].

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

Bertuzzi G.;
2020

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.
2020
Bertuzzi G., McLeod D., Mohr L.-M., Jorgensen K.A. (2020). Organocatalytic Enantioselective 1,3-Dipolar [6+4] Cycloadditions of Tropone. CHEMISTRY-A EUROPEAN JOURNAL, 26(67), 15491-15496 [10.1002/chem.202003329].
Bertuzzi G.; McLeod D.; Mohr L.-M.; Jorgensen K.A.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/829850
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