Chiral tertiary propargylic alcohols via Pd-catalyzed carboxylative kinetic resolution

A highly efficient Pd/H+-cocatalyzed kinetic resolution reaction of tertiary propargylic alcohols has been reported. The method provides an efficient approach to prepare a series of propargylic alcohols bearing a chiral quaternary stereocenter in good yields and remarkable enantioselectivities (93–>99% ee) under mild and operationally simple reaction conditions tolerating a broad range of functional groups. The practicality of this method has been demonstrated via the 4-gram-scale synthesis of chiral propargylic alcohol (S)-1a.