Asymmetric "Acetylenic" [3+2] Cycloaddition of Nitrones Catalyzed by Cationic Chiral PdII Lewis Acid

Kazuya Honda; Koichi Mikami

doi:10.1002/asia.201801016

Asymmetric "Acetylenic" [3+2] Cycloaddition of Nitrones Catalyzed by Cationic Chiral Pd^II Lewis Acid

Chem Asian J. 2018 Oct 4;13(19):2838-2841. doi: 10.1002/asia.201801016. Epub 2018 Aug 29.

Authors

Kazuya Honda¹, Koichi Mikami¹

Affiliation

¹ Department of Applied Chemistry, Tokyo Institute of Technology, Tokyo, 152-8552, Japan.

PMID: 30079984
DOI: 10.1002/asia.201801016

Abstract

Highly enantioselective [3+2] cycloaddition of ynones and nitrones has been developed. Very bulky ligand, DTBM-SEGPHOS, was used for an effective asymmetric induction over distal reaction centers on the linear ynone dipolarophile and for prevention of Pd^II catalyst deactivation by coordination of the nitrones. The reaction has wide scope of substrates in both ynones and nitrones.

Keywords: alkynes; computational chemistry; cycloaddition; palladium; synthetic methods.