Diastereoselective Preparation of (R)- and (S)-2-Methoxy-2-phenylpent-3-ynoic Acids and Their Use as Reliable Chiral Derivatizing Agents

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• 作者：Salvador P茅rez-Estrada ; Pedro Joseph-Nathan ; Hugo A. Jim茅nez-V谩zquez ; Manuel E. Medina-L贸pez ; Francisco Ayala-Mata ; L. Gerardo Zepeda
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：February 17, 2012
• 年：2012
• 卷：77
• 期：4
• 页码：1640-1652
• 全文大小：538K
• 年卷期：v.77,no.4(February 17, 2012)
• ISSN：1520-6904

文摘

Benzoyl-S,O-acetals 1a and 1b were used as chiral auxiliaries to achieve the diastereoselective preparation of both enantiomers of 2-methoxy-2-phenylpent-3-ynoic acids (MPPAs). The latter were condensed with several chiral secondary alcohols and some primary amines to evaluate their potential as chiral derivatizing agents (CDAs). The ¹H NMR spectra of the corresponding esters and amides showed strong consistency with the absolute configuration of the carbinol and amine moieties, whose observed 螖未L₁ and 螖未L₂ values were in the ranges of 0.1鈥?.4 and 0.02鈥?.12 ppm, respectively.