178180-47-7

Basic information

• Product Name: 2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (R)-2-phenyl-propyl ester
• CAS NO: 178180-47-7
• Molecular Weight: 291.39
• Mol File: 178180-47-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (R)-2-phenyl-propyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (R)-2-phenyl-propyl ester(178180-47-7)
• EPA Substance Registry System: 2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (R)-2-phenyl-propyl ester(178180-47-7)

Safety Data

• Hazardous Substances Data: 178180-47-7(Hazardous Substances Data)

Upstream product

• 1123-85-9 (+)-(R)-2-phenylpropanol 
• 146176-60-5 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl chloride 
• 1123-85-9 (RS)-2-phenyl-1-propanol 

Downstream Products

• 121840-97-9 (2R,3R)-3-phenyl-butane-1,2-diol 

Relevant articles and documents

Experimental and theoretical studies of the internal stereodifferentiation occurring during the lithiation of β-stereogenic alkyl carbamates. Kinetic resolutions by (-)-sparteine-mediated deprotonation

The deprotonation of β-stereogenic alkyl carbamates 8 with sec-butyllithium/TMEDA proceeds kinetically controlled with differentiation between the diastereotopic protons at the α-methylene group. The lithium intermediates 9A and 9B are trapped by electrophiles to give carboxylic acid esters 10A/ B and stannanes 11A/B, 13A/B. The diastereomeric ratio of A to B is independent of the electrophile. The highest efficiency is achieved with β-aryl-β-alkyl-substituted starting compounds 8d-f. The trends in the experimentally observed diastereoselectivities are reflected by the results of semiempirical PM3 calculations on the transition states of the deprotonation reaction. - As a result of double stereodifferentiation, application of the chiral base sec-butyllithium/(-)-sparteine gives rise to efficient kinetic resolution of racemic alkyl carbamates. VCH Verlagsgesellschaft mbH, 1996.