Asymmetric Hydroamination

  • Alexander L. Reznichenko
  • Agnieszka J. Nawara-Hultzsch
  • Kai C. Hultzsch
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 343)


The direct addition of amine N–H bonds across an unsaturated carbon–carbon linkage gives fast and highly atom-economical access to amines. This review provides an overview of the most effective stereoselective methods using various catalyst systems based on alkali, alkaline earth, and transition metals, as well as enzymatic and organocatalytic approaches. Except for a few sporadic examples in the last century, this field has evolved primarily over the last decade. Catalyst systems have reached enantioselectivities exceeding 90% ee for many substrate classes, but significant challenges remain, in particular in the stereoselective intermolecular hydroamination of unactivated alkenes.


Alkenes Amines Asymmetric catalysis Brønsted acid catalysis Heterofunctionalization Hydroamination Nitrogen heterocycles Transition metal catalysis 





































Diastereomer ratio




Enantiomer excess
















Potassium hexamethyldisilazide potassium bis(trimethylsilyl)amide


Lithium diisopropylamide


p-Methoxy benzenesulfonyl






Mesityl 2,4,6-trimethylphenyl




Molecular sieves








N-Methylmorpholine N-oxide


Turnover frequency


Phenylalanine ammonia lyase


Protecting group








Room temperature










Trifluoromethanesulfonyl (triflyl)


Trifluoroacetic anhydride












Tosyl 4-toluenesulfonyl





Generous financial support by the National Science Foundation through a NSF CAREER Award (CHE 0956021) is gratefully acknowledged.


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Copyright information

© Springer-Verlag Berlin Heidelberg 2013

Authors and Affiliations

  • Alexander L. Reznichenko
    • 1
  • Agnieszka J. Nawara-Hultzsch
    • 1
  • Kai C. Hultzsch
    • 1
  1. 1.Department of Chemistry and Chemical BiologyRutgers, The State University of New JerseyPiscatawayUSA

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