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A Phosphine‐Catalyzed Novel Asymmetric [3+2] Cycloaddition of C,N‐Cyclic Azomethine Imines with δ‐Substituted Allenoates
Author(s) -
Wang De,
Lei Yu,
Wei Yin,
Shi Min
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405191
Subject(s) - synthon , cycloaddition , phosphine , catalysis , substrate (aquarium) , chemistry , combinatorial chemistry , scope (computer science) , medicinal chemistry , organic chemistry , computer science , oceanography , geology , programming language
Catalytic asymmetric [3+2] cycloadditions of C,N‐cyclic azomethine imines with δ‐substituted allenoates have been developed in the presence of ( S )‐Me‐f‐KetalPhos, affording functionalized tetrahydroquinoline frameworks in good yields with high diastereo‐ and good enantioselectivities under mild condition. The substrate scope has been also examined. This is the first time that δ‐substituted allenoates have been applied as a δ,γ‐CC bond participated C 2 synthon in asymmetric synthesis.