The present article describes the recent catalytic asymmetric methods developed in our group to access enantioenriched chiral aldehydes. We are generally aiming at developing complementary strategies based on either homogeneous organometallic catalysts or amino-catalysts and sometimes on a combination of both. Recent successes comprise a perfectly redox-economical iridium-catalyzed asymmetric isomerization of primary allylic alcohols under very mild conditions and the development of a transition metal-catalyzed anti-Markovnikov asymmetric hydroboration of 1,1-disubstituted olefins. The developments of these two processes along with preliminary mechanistic investigations are presented herein.