1,5-Rhodium Shift in Rearrangement of N-Arenesulfonylazetidin-3-ols into Benzosultams
1,5-Rhodium Shift in Rearrangement of N-Arenesulfonylazetidin-3-ols into Benzosultams
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DOI：
10.1021/ja410910s
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发表时间：
2013-12-25
影响因子：
15
通讯作者：
Murakami, Masahiro
中科院分区：
文献类型：
--
作者：
Ishida, Naoki;Shimamoto, Yasuhiro;Murakami, Masahiro
通过N-芳烃磺酰基氮杂环丁烷-3-醇的铑催化重排反应，从α-氨基酸开始合成对映体纯形式的苯磺内酰胺。在机理上，该反应涉及通过β-碳消除的C-C键裂解和通过1，5-铑移位的C-H键裂解。
Benzosultams are synthesized in an enantiopure form starting from alpha-amino acids through a rhodium-catalyzed rearrangement reaction of N-arenesulfonylazetidin-3-ols. Mechanistically, this reaction involves C-C bond cleavage by beta-carbon elimination and C-H bond cleavage by a 1,5-rhodium shift.