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Asymmetric Organocatalytic Stepwise [2+2] Entry to Tetra‐Substituted Heterodimeric and Homochiral Cyclobutanes
Author(s) -
Nielsen Alex J.,
Jenkins Hilary A.,
McNulty James
Publication year - 2016
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.201601842
Subject(s) - cyclobutanes , tetra , chemistry , cycloaddition , amine gas treating , stereochemistry , enantiomeric excess , enantiomer , organocatalysis , biocatalysis , enantioselective synthesis , combinatorial chemistry , catalysis , organic chemistry , medicinal chemistry , reaction mechanism
An asymmetric synthesis of tetra‐substituted cyclobutanes involving an organocatalytic, stepwise [2+2]‐cycloaddition is described. The secondary‐amine‐catalyzed method allows for the hetero‐dimerization of two different cinnamic‐acid‐derived sub‐units, opening a novel one‐step assembly to densely functionalized, head‐to‐tail coupled dimeric cyclobutanes in high enantiomeric excess. A series of selective synthetic interconversions in these sensitive cycloadducts is also described.
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