Asymmetric [4+1] Cycloadditions of N-Thioacylimines and Sulfur Ylides

Asymmetric [4+1] Cycloadditions of N-Thioacylimines and Sulfur Ylides
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N-硫代酰亚胺和硫叶立德的不对称[4 1]环加成

DOI:
10.1002/adsc.201700445
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发表时间:
2017-08-07
影响因子:
5.4
通讯作者:
Chen, Ying-Chun
Chen, Ying-Chun
中科院分区:
化学2区
文献类型:
--
作者:
Li, Chao;Jiang, Kun;Chen, Ying-Chun

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报道了N-硫代酰亚胺与含D-樟脑支架的硫叶立德原位生成的不对称[4+1]环加成反应。通过添加催化量的(R)-1,1‘-双(2-萘酚),以中等到高的产率和中等到极好的立体选择性(>19:1dr,高达98%ee)提供2-烷基硫代-4,5-二氢噻唑的光谱,显著改善了对映体控制。
An asymmetric [4+1] cycloaddition reaction of N-thioacylimines, generated in situ from alpha-amido sulfones, and sulfur ylides bearing a D-camphor scaffold, is reported. The enantiocontrol was significantly improved by adding catalytic amounts of (R)-1,1 '-bi(2-naphthol), furnishing a spectrum of 2-alkylthio-4,5-dihydrothiazoles in modest to high yields with moderate to excellent stereoselectivity (> 19:1 dr, up to 98% ee).