Preparation and evaluation of nitrene precursors (PhI=NSO2Ar) for the copper-catalyzed aziridination of olefins

N1‐Arylsulfonyl‐N2‐(1‐(1‐naphthyl)ethyl)‐1,2‐diaminocyclohexanes: A New Class of Calcilytic Agents Acting at the Calcium‐Sensing Receptor

“…Moreover, such compounds can be easily prepared from indene by using the copper-catalyzed olefin aziridination procedure previously employed for the synthesis of 5. [17,19,20] Thus, treatment of a slight excess (1.67 equiv) of indene 8 in acetonitrile at 0 8C with 1 equivalent of ((N-4-methoxybenzenesulfonyl)imino)phenyliodane 9 [21] in the presence of 10 mol % copper(i) triflate and molecular sieves provided aziridine 10 in 55 % yield (Scheme 3). The latter was treated with (R,S)-1-(1-naphthyl)ethylamine (11), which attacked uniquely the benzylic position to afford the desired compound 7 in high yield.…”

“…These compounds were prepared as shown in Scheme 5. Thus, reaction of cyclohexene with, this time, ((N-4-nitrobenzenesulfonyl)imino)phenyliodane (22) [21] in the presence of copper(i) triflate gave the N-nosyl-protected aziridine 23. The latter was smoothly opened by (R,S)-1-(1-naphthyl)-ethylamine to afford diamine 24, and the nosyl group was removed by the action of the thiophenol anion.…”

Gold(I)‐Catalyzed Tandem Rearrangement–Nucleophilic Substitution of α‐Acetoxy Alkynyl Oxiranes or Aziridines: Efficient Approach to Furans and Pyrroles

“…[11] As expected, acyloxylated alkynylaziridine 5, synthesized in 41 % yield from the corresponding enyne by using the procedure of Andersson, [12] was efficiently Scheme 4. Gold(I)-catalyzed rearrangement of alkynylaziridines into pyrroles in the presence of alcohols.…”

Copper-catalyzed aziridination of allylglycine derivatives

“…11 The resulting acid 6 and ester 7 were then transformed into compounds 8-12 by standard sequences of deprotection-protection reactions. 13 Several copper complexes were also tested and among those, copper (I) salts appeared to be the more efficient. 14 4 eq.…”

“…The resulting oily residue was purified by flash chromatography on silica gel (heptane-ethyl acetate 95:5) to afford compound 10 (13.0 g, 31.6 mmol, 38%) as a colorless oil. N-(9-phenyl-9H-fluoren-9-yl)amino-3-[N-(2-trimethylsilyl-ethanesulfonyl)aziridin-2′-yl]propanoate (13). To a suspension of activated 3Å molecular sieves (3.75 g) in acetonitrile (25 mL) were successively added compound 10 (2.39 g, 5.8 mmol) and Cu(CH 3 CN) 4 PF 6 (0.63 g, 0.25 eq.).…”