Copper-Catalyzed Enantioselective Formal Hydroamination of Oxa- and Azabicyclic Alkenes with Hydrosilanes and Hydroxylamines

A CuCl/(R,R)-Ph-BPE-catalyzed enantioselective formal hydroamination of oxa- and azabicyclic alkenes with polymethylhydrosiloxane (PMHS) and O-benzoylhydroxylamines has been developed. The efficient and stereoselective net addition of hydrogen and nitrogen atoms provides the corresponding optically...

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Bibliographic Details
Published in:Organic letters 2014-03, Vol.16 (5), p.1498-1501
Main Authors: Miki, Yuya, Hirano, Koji, Satoh, Tetsuya, Miura, Masahiro
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Amination
Azabicyclo Compounds - chemical synthesis
Azabicyclo Compounds - chemistry
Catalysis
Combinatorial Chemistry Techniques
Copper - chemistry
Hydroxylamines - chemistry
Molecular Structure
Stereoisomerism
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Summary:A CuCl/(R,R)-Ph-BPE-catalyzed enantioselective formal hydroamination of oxa- and azabicyclic alkenes with polymethylhydrosiloxane (PMHS) and O-benzoylhydroxylamines has been developed. The efficient and stereoselective net addition of hydrogen and nitrogen atoms provides the corresponding optically active oxa- and azanorbornenyl- and -norbornanylamines in good yields and good enantiomeric ratios.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol5003219