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Synfacts 2013; 9(1): 0057
DOI: 10.1055/s-0032-1317778
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Enantioselective Hydroamination of Allenes

Authors

    Rezensent(en):

  • Hisashi Yamamoto

  • Susumu Oda

Cooke ML, Xu K, Breit B * Albert-Ludwigs-Universität Freiburg, Germany
Enantioselective Rhodium-Catalyzed Synthesis of Branched Allylic Amines by Intermolecular Hydroamination of Terminal Allenes.

Angew. Chem, Int. Ed. 2012;
51: 10876-10879
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Publikationsverlauf

Publikationsdatum:
17. Dezember 2012 (online)

 
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Key words

rhodium - hydroamination - allenes

Significance

Despite the versatility of α-chiral ­allylic amines, synthetic methods to access them have been underdeveloped. The authors reported the first example of the enantioselective inter­molecular hydroamination of mono-substituted ­allenes.


 

Comment

A variety of substituted anilines, even bearing unprotected alcohol and indole moieties, were employed to give good yields and high enantioselectivities. Further mechanistic study is desirable to explain the regioselectivity of the hydrometalation step.


 

 


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