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Enantioselective, Stereodivergent Hydroazidation and Hydroamination of Allenes Catalyzed by Acyclic Diaminocarbene (ADC) Gold(I) Complexes
Author(s) -
Khrakovsky Dimitri A.,
Tao Chuanzhou,
Johnson Miles W.,
Thornbury Richard T.,
Shevick Sophia L.,
Toste F. Dean
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201601550
Subject(s) - hydroamination , enantioselective synthesis , enantiomer , nucleophile , catalysis , chemistry , allylic rearrangement , combinatorial chemistry , organic chemistry
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.