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The Phenylsulfonyl Group as a Temporal Regiochemical Controller in the Catalytic Asymmetric 1,3‐Dipolar Cycloaddition of Azomethine Ylides
Author(s) -
LópezPérez Ana,
Adrio Javier,
Carretero Juan C.
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200805063
Subject(s) - regioselectivity , cycloaddition , chemistry , pyrrolidine , selectivity , catalysis , 1,3 dipolar cycloaddition , group (periodic table) , combinatorial chemistry , organic chemistry
Controlling the regioselectivity : The phenylsulfonyl group controlled the regioselectivity in the title reaction to afford pyrrolidine‐2,3‐dicarboxylates with good regioselectivity and high exo selectivity and enantioselectivity (see scheme). The products are precursors to substituted pyrrolidines and pyrrolines that are not attainable by direct 1,3‐dipolar cycloadditions with typical acrylates.