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Practical Asymmetric Synthesis of a Bicyclic Pyrrolidinol

有机合成与工艺文献分享 2025-04-25 08:50
文章摘要
本文介绍了一种双环吡咯烷醇的不对称合成方法。研究背景是基于早期从焦谷氨酸乙酯出发的六步合成路线收率不足4%的问题。研究目的是开发一种以N-Boc-trans-4-羟基-L-脯氨酸甲酯为起始原料的立体选择性合成路线。研究结果表明，使用Et3N·3HF进行脱氧氟化反应条件温和且能避免烯烃副产物的形成，优化后的α-烷基化反应立体选择性超过100:1，并通过酸介导的氨缩醛氮活化成功去除了Seebach辅助基团。文章还探讨了反应机理，发现可以分离得到稳定的季铵盐中间体。
Practical Asymmetric Synthesis of a Bicyclic Pyrrolidinol
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