Stereodivergent Synthesis of Chiral Amino Alcohols by Copper(I) Catalyst

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.