Asymmetric multicomponent domino reactions and highly enantioselective conjugated addition of thiols to alpha,beta-unsaturated aldehydes

Mauro Marigo; Tobias Schulte; Johan Franzén; Karl Anker Jørgensen

doi:10.1021/ja055291w

Asymmetric multicomponent domino reactions and highly enantioselective conjugated addition of thiols to alpha,beta-unsaturated aldehydes

J Am Chem Soc. 2005 Nov 16;127(45):15710-1. doi: 10.1021/ja055291w.

Authors

Mauro Marigo¹, Tobias Schulte, Johan Franzén, Karl Anker Jørgensen

Affiliation

¹ Danish National Research Foundation, Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark.

PMID: 16277506
DOI: 10.1021/ja055291w

Abstract

An organocatalytic asymmetric multicomponent domino and a conjugated addition reaction to alpha,beta-unsaturated aldehydes are presented. The development is based, first, on an organocatalyzed highly enantioselective nucleophilic thiol addition to the beta-carbon atom in the iminium ion intermediate, followed by an electrophilic amination of the alpha-carbon atom to the enamine intermediate. The multicomponent reactions proceed to give enantiopure amino-thiols in moderate to good yields. Furthermore, the organocatalyzed thiol addition to alpha,beta-unsaturated aldehydes takes place in good yields and excellent enantioselectivities.