Dirhodium(II)-catalyzed C-H amination reaction of (S)-3-(tert-butyldimethylsilyloxy)-2-methylpropyl carbamate: a facile preparation of optically active monoprotected 2-amino-2-methyl-1,3-propanediol.
Dirhodium(II)-catalyzed C-H amination reaction of (S)-3-(tert-butyldimethylsilyloxy)-2-methylpropyl carbamate, which was easily prepared from methyl (S)-2-methyl-3-hydroxypropanoate, proceeded more smoothly than those of their 2-(methoxycarbonyl)propyl derivative to give the corresponding oxazolidinone in excellent yield. The resulting oxazolidinone was converted efficiently into both (R)-monoprotected and (S)-monoprotected 2-amino-2-methyl-1,3-propanediols.
Yakura
Takayuki
T
Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, Toyama, Japan. yakura@pha.u-toyoma.ac.jp
Yoshimoto
Yuya
Y
Ishida
Chisaki
C
D000586:Amination; D002219:Carbamates / Q000737:chemistry*; D002852:Chromatography, Ion Exchange; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D011409:Propylene Glycols / Q000138:chemical synthesis*; D012238:Rhodium / Q000737:chemistry*; D012833:Siloxanes / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism