1997-85-9Relevant articles and documents
Nucleophile-directed selective transformation of cis-1-tosyl-2- tosyloxymethyl-3-(trifluoromethyl)aziridine into aziridines, azetidines, and benzo-fused dithianes, oxathianes, dioxanes, and (thio)morpholines
Kenis, Sara,D'Hooghe, Matthias,Verniest, Guido,Reybroeck, Maaike,Dang Thi, Tuyet Anh,Pham The, Chinh,Thi Pham, Tham,T?rnroos, Karl W.,Van Tuyen, Nguyen,De Kimpe, Norbert
, p. 5966 - 5971 (2013)
A five-step procedure for the synthesis of cis-1-tosyl-2-tosyloxymethyl-3- (trifluoromethyl)aziridine was developed, starting from 1-ethoxy-2,2,2- trifluoroethanol, involving imination, aziridination, ester reduction, hydrogenation, and N-,O-ditosylation steps. Further synthetic elaborations revealed a remarkable difference in the reactivity of cis-1-tosyl-2- tosyloxymethyl-3-(trifluoromethyl)aziridine with respect to aromatic sulfur and oxygen nucleophiles, thus enabling the selective deployment of this versatile substrate as a building block for the synthesis of functionalized aziridines, azetidines, and benzo-fused dithianes, oxathianes, dioxanes, and (thio)morpholines. Copyright
Formylation of fluoroalkyl imines through visible-light-enabled H-atom transfer catalysis: Access to fluorinated α-amino aldehydes
Yang, Sen,Zhu, Shuangyu,Lu, Dengfu,Gong, Yuefa
supporting information, p. 2019 - 2024 (2019/04/10)
A visible-light-enabled catalytic formylation of fluoroalkyl imines is developed. With readily accessible starting materials and organocatalysts, this method provides a general approach to masked fluoroalkyl amino aldehydes. A synergistic catalytic effect
Highly diastereo- and enantioselective vinylogous Mannich reactions of fluorinated aldimines with siloxyfurans
Zhao, Qian-Yi,Yuan, Zhi-Liang,Shia, Min
supporting information; experimental part, p. 637 - 643 (2011/04/25)
A highly regio- and enantioselective asymmetric vinylogous Mannich reaction of readily available fluorinated aldimines bearing a chiral auxiliary [(S)-1-phenylethyl group] with siloxyfurans to afford chiral fluorine-containing γ-butenolide or γ-lactone derivatives has been developed in the presence of silver acetate (10 mol%) and axially chiral phosphine-oxazoline ligand L1 (11 mol%). In most cases, the corresponding fluorinated adducts were obtained in high yields, good to excellent enantiomeric excesses and up to > 20:1 dr.
