Asymmetric decarboxylative Claisen rearrangement reactions of sulfoximine-substituted allylic tosylacetic esters
Asymmetric decarboxylative Claisen rearrangement reactions of sulfoximine-substituted allylic tosylacetic esters
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DOI：
10.1021/jo050747d
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发表时间：
2005-08-19
影响因子：
3.6
通讯作者：
White, AJP
中科院分区：
文献类型：
--
作者：
Craig, D;Grellepois, F;White, AJP
[图]在乙酰基残基上制备了含有多种n -芳基磺酰基亚砜胺的烯丙基乙酸酯，并进行了脱羧Claisen重排反应。重排产物的分离率一般都很好，非对映选择性高达82:18。N-（2,4,6-三异丙基苯基磺酰基）- s -苯基亚砜胺部分的选择性最好。用x射线晶体学确定了主要异构体的立体化学性质。提出了一个解释重排过程的立体化学模型。
[GRAPHICS]Allylic acetate esters containing a variety of N-arylsulfonyl sulfoximines on the acetyl residue have been prepared and submitted to the decarboxylative Claisen rearrangement reaction. Rearranged products were isolated in generally good yields, and diastereoselectivities up to 82:18 have been obtained. The N-(2,4,6-triisopropylphenylsulfonyl)-S-phenyl sulfoximine moiety gave the best selectivity. The stereochemistry of the major isomer was established by X-ray crystallography. A model to explain the stereochemical course of the rearrangement is proposed.