First example of memory of chirality in carbenium ion chemistry
First example of memory of chirality in carbenium ion chemistry
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DOI：
10.1021/ol005795t
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发表时间：
2000-06-15
期刊：
影响因子：
5.2
通讯作者：
Onomura, O
中科院分区：
文献类型：
--
作者：
Matsumura, Y;Shirakawa, Y;Onomura, O
当石墨用作阳极材料时，衍生自L-丝氨酸的N-苯甲酰恶唑烷衍生物6的非柯尔贝反应产生光学活性的N，O-缩醛7。该反应代表碳正离子化学中“手性记忆”的第一个实例。用于阳极的材料对于手性记忆是关键的，发现羧基与甲氧基的取代反应是以反转机理进行的。
[GRAPHICS]The non-Kolbe reaction of N-benzoyloxazolidine derivatives 6 derived from L-serine gave optically active N,O-acetals 7 when graphite was used as an anode material, This reaction represents the first example of "memory of chirality" in carbenium ion chemistry, The material used for the anode was critical for the memory of chirality, The substitution of carboxyl group with methoxyl group was found to proceed with an inversion mechanism.