Stereoselectivity Switch in the Trapping of Polar Organometallics with Andersen’s ReagentAccess to Highly Stereoenriched Transformable Biphenyls

The
trapping of racemic polar carbometallic species with (−)-menthyl
(SS)-p-toluenesulfinate
(Andersen’s reagent) typically proceeds with a very low level
of resolution. In this paper, we describe a strategy that allows
access to highly atropo-enriched and functionalizable biphenyls by
means of Andersen’s reagent under kinetic resolution conditions.
In particular, useful enantiopure 2-iodobiphenyls could be obtained
and were employed in a challenging hypervalent iodine-catalyzed oxidation
reaction.