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Synfacts 2015; 11(9): 0946
DOI: 10.1055/s-0035-1560099
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Hydroamination of Unactivated Internal Olefins

Contributor(s):
Hisashi Yamamoto
,
Yasushi Shimoda
Yang Y, Shi S.-L, Niu D, Liu P, Buchwald SL * Massachusetts Institute of Technology, Cambridge and University of Pittsburgh, USA
Catalytic Asymmetric Hydroamination of Unactivated Internal Olefins to Aliphatic Amines.

Science 2015;
349: 62-66
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Further Information

Publication History

Publication Date:
18 August 2015 (online)

 
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Key words

asymmetric catalysis - hydroamination - alkenes - amines - copper

Significance

Previous hydroaminations of alkenes have been achieved with a restricted range of substrates (for example, styrenes or terminal olefins). Here, the authors succeed in asymmetric hydroamination of nonactivated internal olefins. This system provides ready access to various α-branched chiral amines with high enantio­selectivities (≥96% ee).


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Comment

Electron-rich hydroxylamines are used as aminating reagent to suppress undesired reductions of hydroxylamines. The late-stage modification of pharmaceutical compounds is also demonstrated.


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