Toward the continuous-flow synthesis of chiral tertiary alcohols by enantioselective addition of organozinc reagents to ketones using nanosize isoborneol ligands

摘要: Abstract The catalytic enantioselective addition of different organozinc reagents, such as alkyl or in situ generated phenylzinc derivatives to simple aryl ketones, was accomplished using titanium tetraisopropoxide and chiral ligands derived from trans-1-arenesulfonylamino-2-isoborneolsulfonylamidocyclohexane Frechet-type dendrons with up 2.5 nm diameter, giving the corresponding tertiary alcohols enantioselectivities >99%. A efficient procedure for synthesis used is also described, involving radical thiol dendron styryl-isoborneol derivative.