- Stereoselective Rh-Catalyzed Hydrogenative Desymmetrization of Achiral Substituted 1,4-Dienes
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Highly efficient catalytic stereoselective hydrogenative desymmetrization reactions mediated by rhodium complexes derived from enantiopure phosphine-phosphite (P-OP) ligands are described. The highest performing ligand, which contains a TADDOL-derived phosphite fragment [TADDOL = (2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)], presented excellent catalytic properties for the desymmetrization of a set of achiral 1,4-dienes, providing access to the selective formation of a variety of enantioenriched secondary and tertiary alcohols (six examples, up to 92% ee).
- Fernández-Pérez, Héctor,Lao, Joan R.,Vidal-Ferran, Anton
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supporting information
p. 2836 - 2839
(2016/07/06)
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- Organoboranes. 41. Reaction of Organoboranes with (Dichloromethyl)lithium. Scope and Limitations. Synthesis of Homologated Primary and Secondary Alcohols
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Homologated primary alcohols were prepared from alkylboronic esters by the reaction with (dichloromethyl)lithium, LiCHCl2, followed by KIPBH treatment and oxidation.Homologated secondary alcohols were prepared from representative dialkylborinic esters and trialkylboranes by the reaction with LiCHCl2, followed by treatment with base and oxidation.The yields are generally good with both boronic and borinic esters.On the other hand, the reactions with trialkylboranes exhibited a sensitivity to large steric requirements in the trialkylborane reactant.
- Brown, Herbert C.,Imai, Toshiro,Perumal, P. Thirumali,Singaram, Bakthan
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p. 4032 - 4036
(2007/10/02)
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