53777-08-5Relevant articles and documents
Asymmetric synthesis of tertiary vinyl carbinols by highly stereoselective methylation of α-methyl-β-ketosulfoxides with aluminum reagents
García Ruano, José L.,Rodríguez-Fernández, M. Mercedes,Maestro, M.Carmen
, p. 5701 - 5710 (2004)
Methylation of chiral acyclic α-methyl-β-ketosulfoxides with Me3Al and Me2AlCl is reported. Induced configuration at hydroxylic carbon is mainly controlled by the configuration of the sulfinyl group, with de's higher than 90% in most of the cases regardless the configuration at C-α. The stereochemical pathway seems to be different with both reagents, thus affording a higher stereoselectivity with Me 2AlCl. Pyrolytic desulfinylation and hydrogenolysis of the C-S bond allowed the transformation of the resulting hydroxysulfoxides into interesting optically pure tertiary methyl carbinols.
Very short highly enantioselective Grignard synthesis of 2,2-disubstituted tetrahydrofurans and tetrahydropyrans
Monasterolo, Claudio,Müller-Bunz, Helge,Gilheany, Declan G.
, p. 6531 - 6538 (2019/07/10)
Phenones with elongated chains are shown to be excellent substrates for ligand-promoted asymmetric Grignard synthesis of tertiary alcohols. In turn this enables the simple, short and highly enantioselective (up to 96% ee) preparation of chiral 2,2-disubst
CHIRAL DIAMINE COMPOUNDS FOR THE PREPARATION OF CHIRAL ALCOHOL AND CHIRAL AMINE
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Page/Page column 64, (2015/12/17)
A process for the stereoselective preparation of a chiral alcohol or a chiral amine, the process comprising reacting a first prochiral reactant selected from the group consisting of a ketone, an aldehyde, and an inline, with a second reactant comprising a Grignard reagent, in the presence of a chiral trans-diamim of formula (1) as defined herein. Also provided is the use of the chiral trans-diamine of formula (1) in a Grignard reaction and the chiral trans-diamines per se.