posted on 2018-08-09, 00:00authored byWei Liu, Siraj Z. Ali, Stephen E. Ammann, M. Christina White
We report the development of Pd(II)/cis-aryl sulfoxide-oxazoline
(cis-ArSOX) catalysts for asymmetric C–H alkylation
of terminal olefins with a variety of synthetically versatile nucleophiles.
The modular, tunable, and oxidatively stable ArSOX scaffold is key
to the unprecedented broad scope and high enantioselectivity (37 examples,
avg. > 90% ee). Pd(II)/cis-ArSOX
is unique in its ability to effect high reactivity and catalyst-controlled
diastereoselectivity on the alkylation of aliphatic olefins. We anticipate
that this new chiral ligand class will find use in other transition
metal catalyzed processes that operate under oxidative conditions.