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Pyridine‐ N ‐Oxide as a Mild Reoxidant Which Transforms Osmium‐Catalyzed Oxidative Cyclization
Author(s) -
Donohoe Timothy J.,
Wheelhouse née Gosby Katherine M. P.,
LindsayScott Peter J.,
Glossop Paul A.,
Nash Ian A.,
Parker Jeremy S.
Publication year - 2008
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.200705425
Subject(s) - catalysis , oxidative phosphorylation , chemistry , pyridine , osmium , oxide , combinatorial chemistry , medicinal chemistry , organic chemistry , biochemistry , ruthenium
The PNOman can : The use of pyridine‐ N ‐oxide (PNO) transforms the catalytic oxidative cyclization to include the formation of pyrrolidines from N‐Z‐protected amino alcohols and amino acids (see scheme; Z=PhCH 2 OCO). This new method expands the scope of the oxidative cyclization as illustrated with the synthesis of a range of di‐ and trisubstituted pyrrolidines with complete control of stereochemistry.
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