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A highly substrate‐general synthesis of all‐carbon‐substituted  E ‐ and  Z ‐stereodefined olefins is performed. The method comprises two sets of parallel and stereocomplementary preparations of ( E )‐ and ( Z )‐α,β‐unsaturated esters involving two robust and distinctive reactions: 1) stereocomplementary enol tosylations using readily available TsCl/diamine/(LiCl) base reagents, and 2) stereoretentive Negishi cross‐coupling using the catalysts [Pd(dppe)Cl 2 ] (for  E ) and [Pd(dppb)Cl 2 ] (for  Z ). The present parallel approach is categorized as both type I (convergent approach: 16 examples, 56–87 % yield) and type II (divergent approach: 18 examples, 70–95 % yield). The obtained ( E )‐ and ( Z )‐α,β‐unsaturated ester scaffolds are successfully transformed into various  E ‐ and  Z ‐stereodefined known and novel olefins (8×2 derivatization arrays). As a demonstration, application to the parallel synthesis of both ( E )‐ and ( Z )‐tamoxifens, a representative motif of all‐carbon‐substituted olefins, is accomplished in a total of eight steps with an overall yield of 58 % (average 93 %) and 57 % (average 93 %), respectively.

chemistryopen

Divergent Synthetic Access to  E ‐ and  Z ‐Stereodefined All‐Carbon‐Substituted Olefin Scaffolds: Application to Parallel Synthesis of ( E )‐ and ( Z )‐Tamoxifens