Catalytic Asymmetric Synthesis of α‐Quaternary Proline Derivatives by 1,3‐Dipolar Cycloaddition of α‐Silylimines | Zendy

HernándezToribio Jorge | Zendy; Padilla Silvia | Zendy; Adrio Javier | Zendy; Carretero Juan C. | Zendy

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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.

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