Catalytic asymmetric aziridination of α,β-unsaturated aldehydes

Deiana, Luca, Dziedzic, Pawel, Zhao, Gui-Ling, Vesely, Jan, Ibrahem, Ismail, Rios, Ramon, Sun, Junliang and Córdova, Armando (2011) Catalytic asymmetric aziridination of α,β-unsaturated aldehydes. Chemistry - A European Journal, 17 (28), 7904-7917. (doi:10.1002/chem.201100042). (PMID:21611987)

Abstract

The development, scope, and application of the highly enantioselective organocatalytic aziridination of α,β-unsaturated aldehydes is presented. The aminocatalytic azirdination of α,β-unsaturated aldehydes enables the asymmetric formation of β-formyl aziridines with up to >19:1 d.r. and 99% ee. The aminocatalytic aziridination of α-monosubstituted enals gives access to terminal α-substituted-α-formyl aziridines in high yields and up to 99% ee. In the case of the organocatalytic aziridination of disubstituted α,β-unsaturated aldehydes, the transformations were highly diastereo- and enantioselective and give nearly enantiomerically pure β-formyl-functionalized aziridine products (99% ee). A highly enantioselective one-pot cascade sequence based on the combination of asymmetric amine and N-heterocyclic carbene catalysis (AHCC) is also disclosed. This one-pot three-component co-catalytic transformation between α,β-unsaturated aldehydes, hydroxylamine derivatives, and alcohols gives the corresponding N-tert-butoxycarbonyl and N-carbobenzyloxy-protected β-amino acid esters with ee values ranging from 92-99%. The mechanisms and stereochemistry of all these catalytic transformations are also discussed.

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Contributors

Author: Ramon Rios

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