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Stereoselective Synthesis of Pyrrolidines: Catalytic Oxidative Cyclizations Mediated by Osmium
Author(s) -
Donohoe Timothy J.,
Churchill Gwydion H.,
Wheelhouse née Gosby Katherine M. P.,
Glossop Paul A.
Publication year - 2006
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.200603240
Subject(s) - stereoselectivity , chemistry , trifluoroacetic acid , stereospecificity , osmium , alkene , dihydroxylation , catalysis , toluene , organic chemistry , combinatorial chemistry , ruthenium , enantioselective synthesis
A new pathway for oxidative cyclization : N‐protected α‐amino alcohols with distal alkene units cyclize with complete stereoselectivity and stereospecificity to cis ‐pyrrolidines, dependent on the substitution pattern of the starting material. In addition to providing nitrogen‐ and oxygen‐containing heterocycles in good to excellent yields, the catalyst loadings can be reduced to just 0.2 mol % osmium. TMO=Me 3 NO, TFA=trifluoroacetic acid, Ts=toluene‐4‐sulfonyl.