title: Phosphine-Catalyzed [3+2] and [4+3]Annulation Reactions of C,N-Cyclic Azomethine Imines with Allenoates.
abstract: Phosphine-catalyzed [3+2] and [4+3]annulation reactions of C,N-cyclic azomethine imines with allenoates have been developed to give a variety of pharmaceutically attractive tetrahydroisoquinoline derivatives in moderate to excellent yields. The two distinct reaction pathways, [3+2] and [4+3]cyclization, depend on the nature of the nucleophilic phosphine and the allenoate. Generally, for α-alkylallenoates, the reactions always proceed with [3 +2]cyclization as the major pathway no matter what phosphine was used; for α-ArCH2-substituted allenoates, the reaction pathway was controlled by the phosphine catalyst used.
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, People's Republic of China, ; phone: (+86)-10-62731356.
authors.forename: Chengfeng
authors.initials: C
authors.lastname: Jing
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, People's Republic of China, ; phone: (+86)-10-62731356.
authors.forename: Risong
authors.initials: R
authors.lastname: Na
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, People's Republic of China, ; phone: (+86)-10-62731356.
authors.forename: Bo
authors.initials: B
authors.lastname: Wang
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, People's Republic of China, ; phone: (+86)-10-62731356.
authors.forename: Honglei
authors.initials: H
authors.lastname: Liu
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, People's Republic of China, ; phone: (+86)-10-62731356.
authors.forename: Lei
authors.initials: L
authors.lastname: Zhang
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, People's Republic of China, ; phone: (+86)-10-62731356 ; Chemical Industry Press, 13 Qingnianhu South St., Beijing 100011, People's Republic of China.
authors.forename: Jun
authors.initials: J
authors.lastname: Liu
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, People's Republic of China, ; phone: (+86)-10-62731356.
authors.forename: Min
authors.initials: M
authors.lastname: Wang
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, People's Republic of China, ; phone: (+86)-10-62731356.
authors.forename: Jiangchun
authors.initials: J
authors.lastname: Zhong
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
authors.forename: Ohyun
authors.initials: O
authors.lastname: Kwon
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, People's Republic of China, ; phone: (+86)-10-62731356.
authors.forename: Hongchao
authors.initials: H
authors.lastname: Guo
keywords: allenoates; annulation; azomethine imines; catalysis; phosphines