Organoselenium-Catalyzed Enantioselective Synthesis of 2-Oxazolidinones from Alkenes

被引：4
作者：
Cunningham, Carter C. [1 ]
Panger, Jesse L. [1 ]
Lupi, Michela [1 ,2 ]
Denmark, Scott E. [1 ]
机构：
[1] Univ Illinois, Dept Chem, Urbana, IL 61801 USA
[2] Univ Florence, Dept Chem Ugo Schiff DICUS, I-50019 Florence, Italy
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 31期
基金：
美国国家科学基金会;
关键词：
SYN-DICHLORINATION; CHIRAL AUXILIARIES; OXAZOLIDINONES; ALCOHOLS; ACIDS;
D O I：
10.1021/acs.orglett.4c02377
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An operationally simple method for generating enantioenriched 2-oxazolidinones from N-Boc amines and mono- or trans-disubstituted alkenes via chiral organoselenium catalysis is described. Critical to the success of the transformation was the inclusion of triisopropylsilyl chloride (TIPSCl), likely because it sequestered fluoride generated by the oxidant (N-fluorocollidinium tetrafluoroborate) throughout the reaction and suppressed side reactivity. The scope of both the amine and alkene substrates was explored, generating a variety of 2-oxazolidinones in modest to high yields with high enantioselectivities.
引用
收藏
页码：6703 / 6708
页数：6
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