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Phosphine‐Catalyzed Domino Reactions: A Route to Functionalized Bicyclic Skeletons
Author(s) -
Li Erqing,
Huang You
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.201304003
Subject(s) - synthon , bicyclic molecule , annulation , phosphine , catalysis , domino , chemistry , cascade reaction , combinatorial chemistry , organic chemistry , medicinal chemistry
A novel strategy that involves phosphine‐catalyzed sequential [2+3] and [3+2] annulation reactions was developed. In this domino reaction, γ‐substituted allenoates were used as novel C 4 synthons, and the bicyclic cyclopenta[ b ]dihydrofuran derivatives were produced in good to excellent diastereoselectivities and yields under mild conditions. Furthermore, preliminary studies on an asymmetric variant of this reaction proceeded with moderate enantioselectivity.