to afford intermediate 48 in high dr (>20:1). A dDCC was applied here rather than Giese-type addition to acrylate to showcase how a medicinal chemist could use such an approach to easily modulate the length of the carbon chain if desired. Subsequently, 48 can undergo in situ bromination using CEBO/TBAB followed by highly diastereoselectivie Ni-electrocatalytic coupling with 49. This in situ activation/electrocatalytic coupling protocol was modeled after the elegant studies of the Gong group and, in our hands, led to superior conversion relative to the use of chemical reductants (see Supporting Information). Simultaneous Boc and ester reduction yields the target product in only 5 steps from 10, thereby avoiding the need for chiral resolution, pyrophoric reagents (Grignard, LAH x2) and multiple redox manipulations. From a strategic perspective the versatility of installing the arene near the end of the synthesis rather than at the outset is attractive.