tert-Butylsulfonamide. A New Nitrogen Source for Catalytic Aminohydroxylation and Aziridination of Olefins

Abstract

[reaction: see text] The N-chloramine salt of tert-butylsulfonamide has been shown to be an efficient nitrogen source and the terminal oxidant for catalytic aminohydroxylation and aziridination of olefins, resembling closely Chloramine-T by its behavior in these catalytic reactions. The sulfonyl-nitrogen bond in the product or its derivatives is easily cleaved under mild acidic conditions, allowing for facile liberation of the amino group.

3,5‐Bis(trifluoromethyl)phenyl Sulfones for the Highly Stereoselective Julia–Kocienski Synthesis of α,β‐Unsaturated Esters and Weinreb Amides

“…Products 8a, [29] 8b, [30] 8c, [30] 8d, [30] 8e, [30] 8f, [31] 8g, [32] 8h, [33] 8i, [34] 8j, [35] 8k, [29] 8l, [29,36] 10a, [37] 10b, [38] 10c, [39] 10d, [40] 10e, [38] 10f, [41] 10g, [42] 10h, [43] 10i, [43] and 10j [43] have been described previously and gave satisfactory spectroscopic and physical data. Products 8a, 10a and 10d are also commercially available.…”

Bispidine Coordination Chemistry

“…An extensively studied and, depending on the catalyst, efficient and highly stereoselective preparative method is the coppercatalyzed synthesis of aziridines (see Scheme 15) (232-238). The most frequently used nitrene source in these reactions is [N-(p-toluenesulfonyl) imino]phenyliodinane (PhINTs), but others have also been used (239)(240)(241). Interestingly, copper(I) as well as copper(II) complexes have been found to be catalytically active, and copper(II)-catalyzed reactions are of particular interest since the catalysts are air stable.…”

Catalytic Aziridination of Styrene with Copper Complexes of Substituted 3,7‐Diazabicyclo[3.3.1]nonanones

“…These crude mixtures were recrystallized with hexane to produce the pure aziridine products. C 15 Crystal Structure Determination: Crystal data and details of the structure determinations are listed in Table 1. Intensity data were collected at low temperature on a Bruker AXS Smart 1000 diffractometer (Mo-K α , λ ϭ 0.71073 Å , ω-scan).…”