283151-89-3

Basic information

• Product Name: [1R,2R]-(+)-1-hydroxy-2-methyl-1-phenyl-3-heptanone
• Synonyms: [1R,2R]-(+)-1-hydroxy-2-methyl-1-phenyl-3-heptanone
• CAS NO: 283151-89-3
• Molecular Weight: 220.312
• Mol File: 283151-89-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: [1R,2R]-(+)-1-hydroxy-2-methyl-1-phenyl-3-heptanone(CAS DataBase Reference)
• NIST Chemistry Reference: [1R,2R]-(+)-1-hydroxy-2-methyl-1-phenyl-3-heptanone(283151-89-3)
• EPA Substance Registry System: [1R,2R]-(+)-1-hydroxy-2-methyl-1-phenyl-3-heptanone(283151-89-3)

Safety Data

• Hazardous Substances Data: 283151-89-3(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 109-72-8 n-butyllithium 
• 219783-11-6 (2R,3R,1'S,2'S)-(+)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-3-phenylpropanamide 

Relevant articles and documents

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.