146337-04-4Relevant articles and documents
Synthesis of Cyclic Guanidines Bearing N-Arylsulfonyl and N-Cyano Protecting Groups via Pd-Catalyzed Alkene Carboamination Reactions
Peterson, Luke J.,Luo, Jingyi,Wolfe, John P.
supporting information, p. 2817 - 2820 (2017/06/07)
Palladium-catalyzed carboamination reactions of N-allylguanidines bearing cleavable N-cyano or N-arylsulfonyl protecting groups are described. The reactions afford cyclic guanidine products in good yield, and transformations of substrates bearing internal alkenes proceed with high diastereoselectivity. Deuterium labeling studies indicate these transformations proceed via anti-aminopalladation pathways.
Diamine-free lithiation-trapping of N-Boc heterocycles using s-BuLi in THF
Barker, Graeme,Obrien, Peter,Campos, Kevin R.
supporting information; experimental part, p. 4176 - 4179 (2010/11/16)
A diamine-free protocol for the s-BuLi-mediated lithiation-trapping of N-Boc heterocycles has been developed. In the optimized procedure, lithiation is accomplished using s-BuLi in THF at -30 °C for only 5 or 10 min. Subsequent electrophilic trapping or transmetalation-Negishi coupling delivered a range of functionalized pyrrolidines, imidazolidines, and piperazines in 43-83% yield.
Regio- and enantioselective control in the reactions of α-(N-Carbamoyl)alkylcuprates with allylic phosphates
Dieter, R. Karl,Gore, Vinayak K.,Chen, Ningyi
, p. 763 - 766 (2007/10/03)
α-(N-Carbamoyl)alkylcuprates (RCuCNLi or R2CuLi) react with allylic phosphates to afford homoallylic amines in good chemical yields. Regioselectivity is governed by steric factors in both the cuprate reagent and phosphate substrate and systems can be designed to give either the S N2′ or SN2 substitution product cleanly. Excellent enantioselectivities can be achieved with either a scalemic α-di[(N- carbamoyl)-alkyl]cuprate and an achiral phosphate or with a scalemic allylic phosphate and an achiral cuprate reagent.
