937718-01-9Relevant academic research and scientific papers
Synthesis of nitrogenated heterocycles by asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)haloimines
Pablo, Oscar,Guijarro, David,Yus, Miguel
, p. 9181 - 9189 (2013/10/08)
Highly optically enriched, protected, nitrogenated heterocycles with different ring sizes have been synthesized by a very efficient methodology consisting of the asymmetric transfer hydrogenation of N-(tert-butylsulfinyl) haloimines followed by treatment with a base to promote an intramolecular nucleophilic substitution process. N-Protected aziridines, pyrrolidines, piperidines, and azepanes bearing aromatic, heteroaromatic, and aliphatic substituents have been obtained in very high yields and diastereomeric ratios up to >99:1. The free heterocycles can be easily obtained by a simple and mild desulfinylation procedure. Both enantiomers of the free heterocycles can be prepared with the same good results by changing the absolute configuration of the sulfur atom of the sulfinyl group.
Asymmetric synthesis of aziridines by reduction of N-tert-butanesulfinyl α-chloro imines
Denolf, Bram,Leemans, Erika,De Kimpe, Norbert
, p. 3211 - 3217 (2008/02/04)
(Chemical Equation Presented) Reduction of (RS)-N-tert- butanesulfinyl α-halo imines afforded chiral aziridines in good to excellent yields. Upon reduction of (RS)-N-tert-butanesulfinyl α-halo imines with NaBH4 in THF, in
