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Scaleable Synthesis of 1R,5S-Bicyclo[3.1.0]hexan-2-one

有机合成与工艺文献分享 2024-11-30 08:58
文章摘要
本文介绍了1R,5S-Bicyclo[3.1.0]hexan-2-one的可扩展合成方法，该化合物是葡萄糖激酶激活剂的前体。研究由Hodgson等人进行，他们提出了一种高效且高度对映选择性的合成方法，并通过现场生成的前体环氧化物进一步优化了工艺。研究中，TMP的用量被减少到亚化学计量（即催化量），n-BuLi的添加速率成为关键因素。酸敏感性在反应后处理中引起了关注，因此提出了使用酸进行反应混合物淬灭的替代方法。反应的成功关键依赖于pH值，最佳pH范围为10.0-10.5。通过使用二元钾磷酸盐和一元钾磷酸盐调整pH，成功维持了最佳反应条件。
Scaleable Synthesis of 1R,5S-Bicyclo[3.1.0]hexan-2-one
查看文献： A Practical and Scaleable Synthesis of 1R,5S-Bicyclo[3.1.0]hexan-2-one:  The Development of a Catalytic Lithium 2,2,6,6-Tetramethylpiperidide (LTMP) Mediated Intramolecular Cyclopropanation of (R)-1,2-Epoxyhex-5-ene
查看期刊：Organic Process Research & Development
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