91638-69-6Relevant articles and documents
Iterative stereospecific reagent-controlled homologation of pinacol boronates by enantioenriched α-chloroalkyllithium reagents
Blakemore, Paul R.,Burge, Matthew S.
, p. 3068 - 3069 (2008/02/05)
Reaction of pinacol boronates with putative enantioenriched α-chloroalkyllithium species, generated in situ from homochiral α-chloroalkylsulfoxides by sulfoxide ligand exchange with t-BuLi in PhMe at -78 °C, gave chain-extended boronic ester products with generally excellent stereochemical fidelity. Iteration of this stereospecific reagent-controlled homologation (StReCH) process enabled the programmed synthesis of all four stereoisomers of a stereodiad-containing model system (4-benzyl-1,6-diphenylhexan-2-ol) with er ≥ 97:3 in all cases. Copyright