Enantioselective synthesis of 3,4-dihydroisoquinolin-1(2H)-ones by nickel-catalyzed denitrogenative annulation of 1,2,3-benzotriazin-4(3H)-ones with allenes

Motoshi Yamauchi; Masao Morimoto; Tomoya Miura; Masahiro Murakami

doi:10.1021/ja909603j

Enantioselective synthesis of 3,4-dihydroisoquinolin-1(2H)-ones by nickel-catalyzed denitrogenative annulation of 1,2,3-benzotriazin-4(3H)-ones with allenes

J Am Chem Soc. 2010 Jan 13;132(1):54-5. doi: 10.1021/ja909603j.

Authors

Motoshi Yamauchi¹, Masao Morimoto, Tomoya Miura, Masahiro Murakami

Affiliation

¹ Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan.

PMID: 20000760
DOI: 10.1021/ja909603j

Abstract

A denitrogenative annulation reaction of 1,2,3-benzotriazin-4(3H)-ones with allenes catalyzed by a nickel-phosphine complex to produce a variety of substituted 3,4-dihydroisoquinolin-1(2H)-ones in a regioselective manner is described. A highly enantioselective version, as well as structural evidence for the mechanistic course of this reaction, is also presented.