283151-90-6

Upstream product

• 591-51-5 phenyllithium 
• 219783-12-7 [2R,3S,1'S,2'S]-(+)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-butanamide 
• 6668-24-2 2-methyl-1-phenyl-1,3-butanedione 

Downstream Products

• 283151-73-5 [1S,2R,3S]-(+)-2-methyl-1-phenyl-1,3-butanediol 

Relevant academic research and scientific papers

A chemo-enzymatic route to diastereoisomers of 2-methyl-1-phenyl-1,3-butanediol: the dual role of microorganisms

Diastereoisomers (1S,2R,3S)-, (1R,2R,3S)-, (1R,2S,3S)- and (1S,2S,3S)-2-methyl-1-phenyl-1,3-butanediols were prepared by simple and convenient strategies using two different chemo-enzymatic approaches for the reduction of racemic 2-methyl-1-phenyl-1,3-but

Synthesis of valuable chiral intermediates by isolated ketoreductases: Application in the synthesis of α-alkyl-β-hydroxy ketones and 1,3-diols

Regio- and stereoselective reductions of α-substituted 1,3-diketones to the corresponding β-keto alcohols or 1,3-diols by using commercially available ketoreductases (KREDs) are described. A number of α-monoalkyl- or dialkyl-substituted symmetrical as well as non-symmetrical diketones were reduced in high optical purities and chemical yields, in one or two enzymatic reduction steps. In most cases, two or even three out of the four possible diastereomers of α-alkyl-β-keto alcohols were synthesized by using different enzymes, and in two examples both ketones were reduced to the 1,3-diol. By replacing the α-alkyl substituent with the OAc group, 1-keto-2,3-diols, as well as 1,2,3-triols were synthesized in high optical purities. These enzymatic reactions provide a simple, highly stereoselective and quantitative method for the synthesis of different diastereomers of valuable chiral synthons from non-chiral, easily accessible 1,3-diketones.

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.