Enantioselective, Lewis Base-Catalyzed Carbosulfenylation of Alkenylboronates by 1,2-Boronate Migration
A catalytic, enantioselective method for the preparation of chiral, non-racemic, alkylboronic esters bearing two vicinal stereogenic centers is described. The reaction proceeds via a 1,2-migration of a zwitterionic thiiranium-boronate complex to give excl
Tao, Zhonglin,Robb, Kevin A.,Panger, Jesse L.,Denmark, Scott E.
supporting information
p. 15621 - 15625
(2018/11/23)
Iterative stereospecific reagent-controlled homologation of pinacol boronates by enantioenriched α-chloroalkyllithium reagents
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
Blakemore, Paul R.,Burge, Matthew S.
p. 3068 - 3069
(2008/02/05)
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