743430-43-5

Basic information

• Product Name: (2R,3S)-2-hydroxy-1-(2-methoxyphenyl)-3-(N-tert-butoxycarbonylamino)-3-phenyl-1-propanone
• Synonyms: (2R,3S)-2-hydroxy-1-(2-methoxyphenyl)-3-(N-tert-butoxycarbonylamino)-3-phenyl-1-propanone
• CAS NO: 743430-43-5
• Molecular Weight: 371.433
• Mol File: 743430-43-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3S)-2-hydroxy-1-(2-methoxyphenyl)-3-(N-tert-butoxycarbonylamino)-3-phenyl-1-propanone(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-2-hydroxy-1-(2-methoxyphenyl)-3-(N-tert-butoxycarbonylamino)-3-phenyl-1-propanone(743430-43-5)
• EPA Substance Registry System: (2R,3S)-2-hydroxy-1-(2-methoxyphenyl)-3-(N-tert-butoxycarbonylamino)-3-phenyl-1-propanone(743430-43-5)

Safety Data

• Hazardous Substances Data: 743430-43-5(Hazardous Substances Data)

Upstream product

• 177896-09-2 tert-butyl benzylidenecarbamate 
• 224321-19-1 2-hydroxy-1-(2-methoxyphenyl)ethanone 

Downstream Products

• 743430-70-8 2-methoxyphenyl (2R,3S)-2-acetoxy-3-(N-tert-butoxycarbonylamino)-3-phenylpropanoate 
• 743430-69-5 (2R,3S)-2-acetoxy-1-(2-methoxyphenyl)-3-(N-tert-butoxycarbonylamino)-3-phenyl-1-propanone 

Relevant articles and documents

Direct catalytic asymmetric Mannich-type reaction of hydroxyketone using a Et2Zn/linked-BINOL complex: Synthesis of either anti- or syn-β-amino alcohols

Full details of a direct catalytic asymmetric Mannich-type reaction of a hydroxyketone using a Et2Zn/(S,S)-linked-BINOL complex are described. By choosing the proper protective groups on imine nitrogen, either anti- or syn-β-amino alcohol was obtained in good diastereomeric ratio, yield, and excellent enantiomeric excess using the same zinc catalysis. N-Diphenylphosphinoyl (Dpp) imine 3 gave anti-β-amino alcohols in anti/syn = up to >98/2, up to >99% yield, and up to >99.5% ee, while Boc-imine 4 gave syn-β-amino alcohols in anti/syn = up to 5/95, up to >99% yield, and up to >99.5% ee. The high catalyst turnover number (TON) is also noteworthy. Catalyst loading was successfully reduced to 0.02 mol % (TON = up to 4920) for the anti-selective reaction and 0.05 mol % (TON = up to 1760) for the syn-selective reaction. The Et2Zn/(S,S)-linked-BINOL complex exhibited far better TON than in previous reports of catalytic asymmetric Mannich-type reactions. Mechanistic studies to clarify the reason for the high catalyst efficiency as well as transformations of Mannich adducts are also described.