Organocatalytic synthesis of N-Phenylisoxazolidin-5-ones and a one-pot synthesis of beta-amino acid esters.
A novel N-heterocyclic carbene (NHC)-catalyzed C-N bond formation by the reaction of alpha,beta-unsaturated aldehydes and nitrosobenzene to N-phenylisoxazolidin-5-ones, followed by an acid-catalyzed esterification and Bamberger-like rearrangement in a mild one-pot protocol leads to N-p-methoxyphenyl (N-PMP) protected beta-amino acid esters.
Seayad
Jayasree
J
Institute of Bioengineering and Nanotechnology, 31 Biopolis Way, The Nanos, Singapore 138669.
Patra
Pranab Kumar
PK
Zhang
Yugen
Y
Ying
Jackie Y
JY
D000447:Aldehydes / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004951:Esterification; D004952:Esters; D015394:Molecular Structure; D009578:Nitrobenzenes / Q000737:chemistry; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D000596:Amino Acids; D004952:Esters; D009578:Nitrobenzenes; D023303:Oxazolidinones; C036077:nitrobenzene