Abstract
The reaction of N-diphenylphosphinoyl imines 1 with [3-(trimethylsilyl)allyl]dimethylsulfonium bromide (5) in the presence of NaH at room temperature predominantly gave trans-vinylaziridines 4. On the other hand, cis-vinylaziridines 4 were the main products when the preformed ylide prepared from the reaction of [3-(trimethylsilyl)allyl]diphenylsulfonium perchlorate (6) was reacted with the same imines 1 at low temperature. trans-Aziridines were also obtained when imines 1 and sulfinimines 9 were reacted with N,N-dimethylacetamide-2-dimethylsulfonium bromide (7) in the presence of a base, respectively. A mechanistic study showed that the stereochemistry of these reactions was controlled by the reactivity of the imines and ylides. A higher reactivity of imines and ylides favors the formation of cis-aziridines, whereas a lower reactivity leads to trans-products.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
