N-trialkylsilyl bistrifluoromethanesulfonimides (R3SiNTf2) are powerful catalysts for the highly efficient α-amido alkylation reactions of silicon-based nucleophiles

被引:51
作者
Ben Othman, R [1 ]
Bousquet, T [1 ]
Othman, M [1 ]
Dalla, V [1 ]
机构
[1] Univ Havre, Fac Sci & Tech, Unite Rech & Chim Organ & Macromol, F-76058 Le Havre, France
关键词
D O I
10.1021/ol052357j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In situ formed N-trialkylsilyl bistrifluoromethanesulforlimides (R3SiNTf2) species have been shown to efficiently catalyze the nucleophilic substitution reactions of chiral 5-oxypyrrolidin-2-ones by silicon-based nucleophiles. The reaction rates were significantly accelerated in comparison to the cases where the usual triflate catalysts are used. Adducts were obtained in high yields and usual stereoselectivities within short reaction times, and the process was compatible with a semipreparative scale.
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收藏
页码:5335 / 5337
页数:3
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