Diastereoselective intramolecular allyl transfer from allyl carbamate accompanied by 5-endo-trig ring closure

Oskari K Karjalainen; Martin Nieger; Ari M P Koskinen

doi:10.1002/anie.201209443

Diastereoselective intramolecular allyl transfer from allyl carbamate accompanied by 5-endo-trig ring closure

Angew Chem Int Ed Engl. 2013 Feb 25;52(9):2551-4. doi: 10.1002/anie.201209443. Epub 2013 Jan 22.

Authors

Oskari K Karjalainen¹, Martin Nieger, Ari M P Koskinen

Affiliation

¹ Aalto University, School of Chemical Technology, P. O. Box 16100, 00076 AALTO, Finland.

PMID: 23341176
DOI: 10.1002/anie.201209443

Abstract

To All(oc) involved: A palladium-catalyzed formal 5-endo-trig heteroannulation of enones generated in situ from amino acid derived β-keto nitriles has been realized (see scheme; Alloc=allyl carbamate). The reaction proceeds with allyl-group transfer from the carbamate protecting group to generate two new contiguous stereocenters, including one quaternary center, with high selectivity.