Highly diastereoselective epimerization: stereodivergent synthesis of alpha-hydroxy-beta-amino isopentanoic acid.
The high diastereoselectivity of the base-catalyzed epimerization of oxazolidin-2-ones 7 and 8 is shown to depend on the nature of the N-substituent (R group); when R = Bn, the 4,5-trans-product (4S,5R)-9 is formed, whereas when R = H the 4,5-cis-product (4S,5S)-10 is formed, both with >99:1 dr. The successful hydrolysis of the oxazolidin-2-one group in both cis- and trans-derivatives show this to be a stereodivergent route to enantiopure alpha-hydroxy-beta-amino isopentanoic acids (2R,3S)-1 and (2S,3S)-2.
Seo
Woo Duck
WD
Division of Applied Life Science (BK 21 Program), Department of Agricultural Chemistry, Research Institute of Life Science, Gyeongsang National University, 660-701, Korea.
Curtis-Long
Marcus J
MJ
Ryu
Young Bae
YB
Lee
Jin Hwan
JH
Yang
Min Suk
MS
Lee
Woo Song
WS
Park
Ki Hun
KH
D008968:Molecular Conformation; D023303:Oxazolidinones / Q000737:chemistry*; D010421:Pentanoic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D023303:Oxazolidinones; D010421:Pentanoic Acids; C520528:alpha-hydroxy-beta-amino isopentanoic acid