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2005
Amino acids
U 0400
Succinct Synthesis of β-Amino Acids via Chiral Isoxazolines. — An efficient and
synthesis of poly-substituted β-amino acids like (IV) is presented, involving
35- 211 versatile
the stereoselective ring opening of chiral isoxazolines like (I) during nucleophilic
addition towards the C—N double bond followed by oxidative degradation of the so
formed diol unit [cf. (III)] to generate the carboxylate group. The structural diversity
of the isoxazolines is enhanced by alkylation with organomagnesium or organolithium
reagents. Thus, the synthesis of β3- (VII), β2,3- (IV), β3,3- (XI), (XIV) and β2,3,3-amino
acids (XXIII) is smoothly achieved in good yields and selectivities. Additionally, this
synthetic access can successfully be applied to afford cis-β-proline derivatives like
(XXVI). — (FULLER, A. A.; CHEN, B.; MINTER, A. R.; MAPP*, A. K.; J. Am.
Chem. Soc. 127 (2005) 15, 5376-5383; Dep. Chem., Univ. Mich., Ann Arbor,
MI 48109, USA; Eng.) — Mischke
2005
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