Diastereoselective α-Sulfenylation of N-tert-Butanesulfinyl Imidates,The Journal of Organic Chemistry

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Diastereoselective α-Sulfenylation of N-tert-Butanesulfinyl Imidates
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2018-07-16 00:00:00 , DOI: 10.1021/acs.joc.8b01403
Sheng-Tong Niu _{1,

2} , Hui Liu ₁ , Yan-Jun Xu ₁ , Chong-Dao Lu ₁

Affiliation

A diastereoselective α-sulfenylation of chiral α-aryl/alkyl N-tert-butanesulfinyl imidates has been developed. Suitable sulfur electrophiles can be used as sulfenylating reagents to intercept aza-enolates generated from imidate deprotonation, giving α-thiofunctionalized imidates in good yields with high diastereocontrol. This protocol for C–S bond formation can efficiently synthesize enantioenriched 1,2-sulfanyl amine derivatives such as sulconazole.

中文翻译：

非对映选择性的α-亚磺酰ñ -叔-Butanesulfinyl亚氨酸酯

手性的非对映选择性α-α亚磺酰-芳基/烷基ñ -叔-butanesulfinyl亚胺酸酯已经研制成功。合适的硫亲电试剂可用作亚磺酰化试剂，以拦截由亚氨酸酯去质子化生成的氮杂-烯醇酸酯，以高收率和高非对映异构控制性得到α-硫官能化的酰亚胺。该形成C–S键的方案可有效合成对映体富集的1,2-亚硫烷基胺衍生物，如舒康唑。

更新日期：2018-07-16

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