光活性α,α-二取代氨基酸合成的光延反应法
Mitsunobu approach to the synthesis of optically active alpha,alpha-disubstituted amino acids.
作者信息
Green Jonathan E, Bender David M, Jackson Stona, O'Donnell Martin J, McCarthy James R
机构信息
Eli Lilly & Co., Lilly Corporate Center, Indianapolis, Indiana 46285, USA.
出版信息
Org Lett. 2009 Feb 19;11(4):807-10. doi: 10.1021/ol802325h.
Chiral tertiary alpha-hydroxy esters of known stereochemical configuration were transformed to alpha-azido esters by Mitsunobu reaction with HN3. Optimization of this reaction was shown to proceed at room temperature with high chemical yield using 1,1-(azodicarbonyl)dipiperidine (ADDP) and trimethylphosphine (PMe3). Complete inversion of configuration was observed at the alpha-carbon. Several alpha,alpha-disubstituted amino acids were synthesized in high overall chemical yield and optical purity.
具有已知立体化学构型的手性叔α-羟基酯通过与叠氮化氢（HN₃）的 Mitsunobu 反应转化为α-叠氮基酯。结果表明，使用 1,1-(偶氮二羰基)二哌啶（ADDP）和三甲基膦（PMe₃），该反应在室温下以高化学产率进行优化。在α-碳上观察到构型完全翻转。以高总化学产率和光学纯度合成了几种α,α-二取代氨基酸。
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