Highly regio- and stereoselective rearrangement of epoxides to aldehydes catalyzed by high-valent metalloporphyrin complex, Cr(TPP)OTf
Highly regio- and stereoselective rearrangement of epoxides to aldehydes catalyzed by high-valent metalloporphyrin complex, Cr(TPP)OTf
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DOI：
10.1021/ja047104k
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发表时间：
2004-08-11
影响因子：
15
通讯作者：
Takanami, T
中科院分区：
文献类型：
--
作者：
Suda, K;Kikkawa, T;Takanami, T
四苯基卟啉三氟甲磺酸铬(III) Cr(TPP)OTf 在环氧化物区域选择性和立体选择性重排为醛类过程中充当高效且特征性的路易斯酸催化剂。这种 Cr(TPP)OTf 催化反应是一种操作简单且特别方便的方法，用于从 2,3-环氧甲硅烷基醚合成光学活性 β-甲硅烷氧基醛，通过烯丙醇的 Sharpless 环氧化，然后进行甲硅烷基化，可以很容易地以对映体富集形式获得该化合物。
Chromium(III) tetraphenylporphyrin triflate, Cr(TPP)OTf, works as an efficient and characteristic Lewis acid catalyst in the regio- and stereoselective rearrangement of epoxides to aldehydes. This Cr(TPP)OTf-catalyzed reaction is an operationally simple and especially convenient method for synthesizing optically active β-siloxy aldehydes from 2,3-epoxy silyl ethers which are readily available in enantiomerically enriched forms by the Sharpless epoxidation of allylic alcohols followed by silylation.