1013421-14-1Relevant articles and documents
N-HETEROCYCLIC CARBENE CATALYZED SYNTHESIS OF N-PHENYLISOXAZOLIDIN-5-ONE DERIVATIVE AND SYNTHESIS OF β -AMINO ACID ESTER DERIVATIVE
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Page/Page column 48, (2008/12/07)
A process for preparing a N-phenylisoxazolidin-5-one derivative is provided. The process for preparing the N-phenylisoxazolidin-5-one derivative comprises reacting an α, β-unsaturated aldehyde with nitrosobenzene in the presence of a N-heterocyclic carbene (NHC) catalyst. A process for preparing an N-alkoxyphenyl protected β-amino acid ester derivative is further provided. The process for preparing the N-alkoxyphenyl protected β-amino acid ester derivative comprises reacting an α, β-unsaturated aldehyde with nitrosobenzene in the presence of a N-heterocyclic carbene (NHC) catalyst to form a N-phenylisoxazolidin-5-one derivative, and then treating the N-phenylisoxazolidin-5-one derivative with an alcohol in the presence of an acid catalyst. A process for preparing an N-alkoxyphenyl protected β-amino acid ester derivative, comprising treating a N-phenylisoxazolidin-5-one derivative with an alcohol in the presence of an acid catalyst, is also provided.
Organocatalytic synthesis of N-phenylisoxazolidin-5-ones and a one-pot synthesis of β-amino acid esters
Seayad, Jayasree,Patra, Pranab Kumar,Zhang, Yugen,Ying, Jackie Y.
supporting information; experimental part, p. 953 - 956 (2009/04/10)
A novel N-heterocyclic carbene (NHC)-catalyzed C-N bond formation by the reaction of α,β-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 β-amino acid esters.
