316831-31-9Relevant academic research and scientific papers
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.
Advantage of in situ generation of N-arylsulfonyl imines from α-amide sulfones in the phase-transfer-catalyzed asymmetric Strecker reaction
Ooi, Takashi,Uematsu, Yukitaka,Fujimoto, Jun,Fukumoto, Kazuhiro,Maruoka, Keiji
, p. 1337 - 1340 (2007/10/03)
Highly efficient, catalytic enantioselective synthesis of N-arylsulfonyl α-amino nitriles from the corresponding α-amido sulfones has been achieved under toluene-aqueous potassium cyanide biphasic conditions using chiral quaternary ammonium iodide (R,R,R)-1 as an effective phase-transfer catalyst. This Strecker synthesis involving the in situ generation of the reactive N-sulfonyl imines is advantageous for the cyanation of the substrates having primary and secondary alkyl substituents.
Tuning stereoselection in Tethered Biginelli condensations. Synthesis of cis- or trans-1-oxo- and 1-iminohexahydropyrrolo[1,2-c]pyrimidines
McDonald, Andrew I.,Overman, Larry E.
, p. 1520 - 1528 (2007/10/03)
Stereoselection in tethered Biginelli condensations can be tuned to give either the cis or trans stereoisomer of 1-oxohexahydropyrrolo[1,2- c]pyrimidine and 1-iminohexahydropyrrolo[1,2-c]pyrimidine products (see eq 1). With substrates having urea and N-sulfonylguanidine functionality (Schemes 2 and 4), cis stereoselection (4-7:1) is observed when the condensation is accomplished under Knoevenagel conditions, while trans stereoselection (4-20:1) is observed when the condensation is carried out in the presence of polyphosphate ester (PPE). Under both conditions, steroselectivity is highest in the N-sulfonylguanidine series. With substrates bearing a basic guanidine unit, the trans product is formed exclusively under Knoevenagel conditions (Scheme 3).
