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Nosyl aziridines

Jacobsen has utilized [(salen)Co]-catalyzed kinetic resolutions of tenninal epoxides to prepare N-nosyl aziridines with high levels of enantioselectivity [72], A range of racemic aryl and aliphatic epoxides are thus converted into aziridines in a four-step process, by sequential treatment with water (0.55 equivalents), Ns-NH-BOC, TFA, Ms20, and carbonate (Scheme 4.49). Despite the apparently lengthy procedure, overall yields of the product aziridines are excellent and only one chromatographic purification is required in the entire sequence. [Pg.139]

Gold-based catalysis has attracted considerable attention in recent years. A gold-catalyzed aziridination reaction has recently been reported <06JOC5876>. A series of gold catalysts were examined for their ability to catalyze the aziridination of styrene with p-nitrophenylsulfonamide (NsNH2). Styrene and phenyl-substituted styrenes provided the N-nosyl aziridines in good to excellent yields. Cinnamate however provided the aziridine product in only 25% yield. The use of other sulfonamides (e.g. tosyl, trichloroethyl) gave much lower yields of the aziridine product. [Pg.80]

Typically, the stereospecific formation of quaternary centers is as problematic as selective nucleophilic attack at the more substituted carbon of aziridines. Interestingly, a copper mediated methodology has been reported that does both <060L5105>. Although N-tosyl aziridines show favorable results, A-nosyl aziridines gave the best results. The reaction of 89 with a variety of phenols yielded 90 in moderate yields. [Pg.86]

The aziridine ring opening reaction with phenol derivatives using copper(l) acetate (CuOAc)-DBU was reported by Li et al. [51]. Reaction of ethynyl nosyl-aziridine 170 and p-hydroxytyrosine derivative 169 in the presence of DBU (2 equiv.) and a catalytic amount... [Pg.232]

Non-metal catalyzed aziridinations have also been reported. These methods are often more broadly applicable than the metal-catalyzed methods. The use of iV-methylpyrrolidine-2-one hydrotribromide (MPHT) and chloramine-T is an effective route for the synthesis of iV-tosyl aziridines <06MI16>. The aziridination of olefins using i-BuOI and sulfonamides appears to be a general method for aziridination <06CC3337>. The i-BuOI is prepared in situ from t-BuOCl and Nal. This is a broadly applicable method in that a wide variety of sulfonamides (tosyl, nosyl, SES) can be used with roughly equivalent yields. [Pg.81]

In conclusion, the formation of spiro-aziridine only showed efficient selectivity with furan from derivatives. Following a three-step sequence, the (R)-and (5)- spiro-aziridines were prepared in 73% and 30% yield, respectively. Further steps using a N-ortho-nosyl activation/protection system afforded the corresponding endo-spiro-OZTs in overall 20% and 41%, respectively. [Pg.137]

Rhodium perfluorobutyramide, (pfm)4Rh2, has been shown to catalyse the conversion of alkenes to trichloroethoxysulfonyl, nosyl, and tosyl aziridines on reaction with the corresponding sulfonamide and PhI(OAc)2.97... [Pg.304]

As depicted below, alkylation of nosyl amines, such as 36b, can also suffer from competing intramolecular reactions of the Ph3P/DEAD activated alcohol.27 In this instance, rather than giving the expected amino piperidine product 37, alcohol 35 undergoes an intramolecular reaction to form a highly strained aziridine intermediate that then is opened by nosyl amine 36b to give the observed pyrrolidine 38. [Pg.431]

Aziridination of a-trifluoromethyl-substituted acrylates such as 137 can be accomplished with ethyl nosyloxycarbamate. With a weak base such as calcium oxide, a Michael adduct is obtained (138), but with sodium hydride Michael addition is followed by cychzation with extrusion of nosylate ion to give 139. ... [Pg.24]

Ethynyl aziridine 1199 and tyrosine derivative 1200 were coimected to 1201 by ring opening of the aziridine in 90% yield. After removal of the nosyl protecting group, the resulting firee amine was subsequently coupled with A-Cbz valine (for... [Pg.228]


See other pages where Nosyl aziridines is mentioned: [Pg.260]    [Pg.94]    [Pg.620]    [Pg.5]    [Pg.16]    [Pg.167]    [Pg.65]    [Pg.260]    [Pg.94]    [Pg.620]    [Pg.5]    [Pg.16]    [Pg.167]    [Pg.65]    [Pg.377]    [Pg.137]    [Pg.307]    [Pg.307]    [Pg.57]    [Pg.57]    [Pg.307]    [Pg.71]    [Pg.95]    [Pg.532]    [Pg.2041]    [Pg.174]   
See also in sourсe #XX -- [ Pg.65 ]




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Nosylation

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