催化性有氧氧氧化p-甲基 (PMB) 乙醇到化物或酸盐
Qian Zhang1, Hui Qian1, Shengming Ma1,2
1Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai, 200433, China.
一种新的有氧氧化方法有效地使用铁和TEMPO催化剂将p-甲基乙烯转化为化物或酸. 这种温和的过程保留了敏感的性中心和功能组,使复杂的合成成为可能.
科学领域:
- 有机化学 有机化学
- 催化剂是一种催化剂.
- 合成方法论 合成方法论
背景情况:
- p-Methoxybenzyl (PMB) 乙烯是常见的保护组,用于酒精.
- 氧化PMB乙烯对于碳化合物的降解保护和合成至关重要.
- 现有的方法可能缺乏选择性,需要恶劣的条件,或导致奇拉中心的种族化.
研究的目的:
- 开发一种高效且高度选择性的p-甲基乙烯的有氧氧化.
- 为了在温和的条件下实现与各种功能组和敏感的立体中心相容的氧化.
- 为了证明该方法在合成天然产品的关键中间体中的实用性.
主要方法:
- 氧化氧化催化由铁酸非酸盐 (Fe(NO3) 3·9H2O) 和TEMPO (2,2,6,6-四甲基酸二氧化) 催化.
- 在空气 (氧气) 的存在下,在25°C进行反应.
- 与多种功能组 (阿达曼,以太,基,基) 和光学活性基质的兼容性研究.
主要成果:
- 在p-甲基乙烯氧化成化物和酸盐的高产量和选择性.
- 在敏感基板中维护光学活动和α-chiral中心.
- 对各种功能组和其他基保护组的耐受性.
- 在合成 (R) - tert-butyldimethylsilyl hept-1-en-6-yn-4-yl 以太的成功应用.
结论:
- 已经建立了一个新的,高效和选择性的PMB乙烯的催化有氧氧化协议.
- 该方法提供了温和的反应条件,广泛的功能组兼容性和优秀的立体化学控制.
- 该协议为有机合成提供了有价值的工具,特别是在复杂分子的总合成中.
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