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Enantioselective,Stereodivergent Hydroazidation and Hydroamination of Allenes Catalyzed by Acyclic Diaminocarbene (ADC) Gold(I) Complexes |
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| Authors: | Dimitri A Khrakovsky Prof?Dr Chuanzhou Tao Miles W Johnson Richard T Thornbury Sophia L Shevick Prof?Dr F Dean Toste |
| Institution: | 1. Department of Chemistry, University of California, Berkeley, Berkeley, CA, USA;2. School of Chemical Engineering, Huaihai Institute of Technology, Lianyungang, P.R. China;3. Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA, USA |
| Abstract: | The gold‐catalyzed enantioselective hydroazidation and hydroamination reactions of allenes are presented herein. ADC gold(I) catalysts derived from BINAM were critical for achieving high levels of enantioselectivity in both transformations. The sense of enantioinduction is reversed for the two different nucleophiles, allowing access to both enantiomers of the corresponding allylic amines using the same catalyst enantiomer. |
| Keywords: | acyclic diaminocarbene enantioselective synthesis gold catalysis hydroamination hydroazidation |