Shi S.-L, Wong ZL, Buchwald SL * Massachusetts Institute of Technology, Cambridge,
USA
Copper-Catalysed Enantioselective Stereodivergent Synthesis of Amino Alcohols.
Nature 2016;
532: 353-356
Key words
copper catalysis - amino alcohols - hydrosilylation - hydroamination - stereodivergent
synthesis
Significance
The authors report the stereodivergent synthesis of amino alcohols bearing up to three
contiguous stereocenters by copper-catalyzed hydrosilylation/hydroamination from readily
available enals or enones. The reported method allows access to all stereoisomers
by choosing the (E)/(Z)-isomer of the substrate and the (R)/(S)-enantiomer of the ligand.
Comment
Various enals, enones, and aminating reagents, especially those containing acetals,
phenols, esters and heteroaromatics, were tolerated in the reported method, affording
chiral amino alcohols in good to high yield with excellent diastereo- and enantioselectivity.
Under the ligand exchange protocol, eight stereoisomers were obtained in moderate
to good yield with excellent stereoselectivity.
