112294-91-4Relevant articles and documents
Reformatsky-type reaction of chiral nonracemic α-bromo-α′ -sulfinyl ketones with aldehydes. Synthesis of enantiomerically pure 2-methyl-1,3-diol moieties
Obringer, Michel,Colobert, Francoise,Neugnot, Benjamin,Solladie, Guy
, p. 629 - 632 (2003)
Figure presented Chiral nonracemic α-bromo-α′-sulfinyl ketones were shown to react with aldehydes in the presence of Sml2 in a Reformatsky-type reaction to give the corresponding adduct with excellent syn diastereoselectivity. Further reduction
Asymmetric aldol reactions using (S,S)-(+)-pseudoephedrine-based amides: Stereoselective synthesis of α-methyl-β-hydroxy acids, esters, ketones, and 1,3-syn and 1,3-anti diols
Vicario, Jose L.,Badia, Dolores,Dominguez, Esther,Rodriguez, Monica,Carrillo, Luisa
, p. 3754 - 3759 (2007/10/03)
A very efficient method for performing stereoselective aldol reactions is reported. The reaction of (S,S)-(+)-pseudoephedrine-derived propionamide enolates with several aldehydes yielded exclusively one of the four possible diastereomers in good yields, although transmetalation of the firstly generated lithium enolate with a zirconium(II) salt, prior to the addition of the aldehyde, is necessary in order to achieve high syn selectivity. The so-formed syn-α-methyl-β-hydroxy amides were transformed into other valuable chiral nonracemic synthons such as α-methyl-β-hydroxyacids, esters, and ketones. Finally, a stereocontrolled reduction procedure starting from the so-obtained α-methyl-β-hydroxy ketones has been developed allowing the synthesis of either 1,3-syn- or 1,3-anti-α-methyl-1,3-diols in almost enantiopure form by choosing the appropriate reaction conditions.
