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Catalytic Asymmetric Synthesis of α‐Quaternary Proline Derivatives by 1,3‐Dipolar Cycloaddition of α‐Silylimines
Author(s) -
HernándezToribio Jorge,
Padilla Silvia,
Adrio Javier,
Carretero Juan C.
Publication year - 2012
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.201203828
Subject(s) - proline , cycloaddition , catalysis , trimethylsilyl , chemistry , combinatorial chemistry , quaternary , medicinal chemistry , organic chemistry , computer science , amino acid , biology , biochemistry , paleontology
Going pro : The title reaction between α‐silylimines and activated olefins proceeds in the presence of a Cu I /DTBM‐Segphos catalyst system with excellent diastereoselectivity and enantioselectivity. This process provides straightforward access to highly enantioenriched 5‐unsubstituted α‐quaternary proline derivatives. TMS=trimethylsilyl, DTBM‐Segphos=5,5′‐bis[di(3,5‐di‐ tert ‐butyl‐4‐methoxyphenyl)phosphino]‐4,4′‐bi‐1,3‐benzodioxole.