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Phosphine‐Catalyzed [3+2] and [4+3] Annulation Reactions of C,N‐Cyclic Azomethine Imines with Allenoates
Author(s) -
Jing Chengfeng,
Na Risong,
Wang Bo,
Liu Honglei,
Zhang Lei,
Liu Jun,
Wang Min,
Zhong Jiangchun,
Kwon Ohyun,
Guo Hongchao
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100831
Subject(s) - annulation , phosphine , chemistry , catalysis , nucleophile , organocatalysis , medicinal chemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis
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‐ArCH 2 ‐substituted allenoates, the reaction pathway was controlled by the phosphine catalyst used.