Abstract
The stereospecific reagent-controlled homologation (StReCH) of boronic esters using enantioenriched main-group chiral carbenoid reagents generated by sulfoxide–metal exchange (SMX) is described. The StReCH concept, which upon iteration allows for the programmed installation of multiple stereogenic centers into a growing polysubstituted alkyl chain, is defined and contrasted against the stereoinductive substrate-controlled Matteson homologation. The scope and limitations of SMX-based StReCH using three different carbenoid classes, α-chloroalkylmetals, α - lithiooxiranes, and α-metalated α - (oxycarbonyl)alkyl compounds, are presented, and applications in target directed synthesis are highlighted. Stereoselective syntheses of the sulfoxide carbenoid precursors are also described, and mechanistic aspects of all processes involved are detailed.
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