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Stereoselective Alkylation of Oxathiazinane N,
Heterocycles ( IF 0.6 ) Pub Date : 2020-10-28 , DOI: 10.3987/com-20-s(k)29
Takayuki Yakura , Eri Tanaka , Mai Okada , Chiaki Hirosawa , Narumi Noda , Tomoya Fujiwara

Stereoselective construction of aza-quaternary carbon centers was achieved using the alkylation of oxathiazinane N,O-ketals prepared by Rh(II)-catalyzed C–H amination of sulfamates. The addition of alkyl Grignard reagents into N,O-ketals in the absence of any Lewis acid proceeded stereoselectively to provide the corresponding alkylated products with an aza-quaternary carbon center in high yields. The obtained product could be converted into an α-amino alcohol derivative, which is a potential synthetic intermediate for sphingofungin F and its derivatives.

中文翻译:

Oxathiazinane N,的立体选择性烷基化

氮杂-季碳中心的立体选择性结构是通过由Rh(II)催化的氨基磺酸C-H氨化反应制备的草并恶嗪烷N O-缩酮实现的。在不存在任何路易斯酸的情况下,将烷基格氏试剂添加到N O-缩酮中进行立体选择,从而以高收率向相应的烷基化产物提供了氮杂-季碳中心。所获得的产物可以转化为α-氨基醇衍生物,其是鞘氨醇单蛋白F及其衍生物的潜在合成中间体。
更新日期:2020-10-28
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