通过 Mn 介导的自由基对手性 γ-腙酯的加成反应合成 γ-氨基酯。
Synthesis of gamma-amino esters via Mn-mediated radical addition to chiral gamma-hydrazonoesters.
机构信息
Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, USA.
出版信息
Org Lett. 2009 Mar 5;11(5):1095-8. doi: 10.1021/ol802932v.
Highly stereoselective Mn-mediated couplings of alkyl iodides with chiral N-acylhydrazones bearing ester functionality afford a series of gamma-hydrazino esters, including gamma-substituted, alpha,gamma-disubstituted, and alpha,alpha,gamma-trisubstituted examples. In contrast to prior work with chiral N-acylhydrazones, high stereoselectivity was observed even in the absence of Lewis acid. Microwave-assisted acylation with trifluoroacetic anhydride and reductive N-N bond cleavage provided the gamma-amino ester functionality in a synthetically useful N-TFA-protected form.
高度对映选择性的锰介导的手性 N-酰基腙的烷基碘化物偶联反应，得到一系列γ-酰基腙酯，包括γ-取代、α，γ-二取代和α，α，γ-三取代的实例。与先前使用手性 N-酰基腙的工作相比，即使在没有路易斯酸的情况下也观察到了高对映选择性。用三氟乙酸酐进行微波辅助酰化和还原 N-N 键裂解，以合成上有用的 N-TFA 保护形式提供了γ-氨基酯官能团。
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