112294-91-4

Upstream product

• 73255-30-8 (+/-)-3-(1-hydroxypropyl)but-3-en-2-one 
• 917-54-4 methyllithium 
• 219783-13-8 [2R,3S,1'S,2'S]-(+)-N-(2'hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-pentanamide 
• 503830-59-9 (+)-(3R,4S,R_S)-1-(tert-butylsulfinyl)-4-hydroxy-3-methylhexan-2-one 

Relevant academic research and scientific papers

Reformatsky-type reaction of chiral nonracemic α-bromo-α′ -sulfinyl ketones with aldehydes. Synthesis of enantiomerically pure 2-methyl-1,3-diol moieties

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

A new access to enantiopure syn- and anti-2-methyl-1,3-diol moieties from chiral nonracemic α-bromo α′-sulfinyl ketones promoted by samarium diiodide

syn- and anti-2-Methyl-1,3-diols have been prepared by a two-step sequence that involves a SmI2-promoted stereoselective Reformatsky addition of chiral nonracemic α-bromo α′-sulfinyl ketones to various aldehydes followed by stereoselective redu

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

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.

Asymmetric Reduction of α-Methylene Ketones by Using Fermenting Baker's Yeast. Preparation of Optically Active β-Hydroxy α-Methyl Ketones

Asymmetric reduction of 4-hydroxy-3-methylenealkan-2-ones with baker's yeast afforded (3R,4S)-4-hydroxy-3-methylalkan-2-ones in >98percent ee and the (3R,4R) isomers in 67 -> 98 percent ee in ratios of 1:1-2.