Asymmetric synthesis of beta2-amino acids: 2-substituted-3-aminopropanoic acids from N-acryloyl SuperQuat derivatives.
作者： James E. Beddow , Stephen G. Davies , Kenneth B. Ling , Paul M. Roberts , Angela J. Russell
DOI: 10.1039/B707689D
关键词:
摘要: Conjugate addition of lithium dibenzylamide to (S)-N(3)-acryloyl-4-isopropyl-5,5-dimethyloxazolidin-2-one (derived from L-valine) and alkylation the resultant β-amino enolate provides, after deprotection, a range (S)-2-alkyl-3-aminopropanoic acids in good yield high ee. Alternatively, via complementary pathway, conjugate secondary amides (S)-N(3)-(2′-alkylacryloyl)-4-isopropyl-5,5-dimethyloxazolidin-2-ones, diastereoselective protonation with 2-pyridone, subsequent deprotection furnishes (R)-2-alkyl- (R)-2-aryl-3-aminopropanoic Additionally, boron-mediated aldol reaction N-acyl oxazolidinones is highly method for synthesis β-amino-β′-hydroxy oxazolidinones.
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