An improved two-resin method for the cleavage of tertiary amines from REM resin

Reductive amination with a scavenger: The most “combinatorial” of two-component reactions

“…There are rare examples of reductive amination of furfural and its aldehyde derivatives (including 5-aryl derivatives IE [13][14][15]), but this subject has not yet been studied systematically. Interestingly, the resulting…”

Isothiouronium-derived simple fluorescent chemosensors of anions

“…The latter unit is well known as one of the key parts often used in catalytic reagents and chiral receptors. 11 In the initial step of this research, the synthesis of the naphthalene-isothiouronium dyad 1 was carried out as outlined in Scheme 1; 2-bromomethylnaphthalene 3 was converted to the 2-aminomethyl derivative 4 12 via Gabriel synthesis, 13 during which 3 was allowed to react with potassium phthalimide, followed by treatment with NH 2 NH 2 ؒH 2 O. The condensation of 4 with MeNCS in CHCl 3 gave the corresponding thiourea derivative 5 in 68% yield, which was amenable to reaction with 1.1 equiv.…”

“…Compound 4 12 (300 mg, 1.91 mmol) was dissolved in CHCl 3 (7 mL). After a CHCl 3 solution (3 mL) containing MeNCS (419 mg, 5.73 mmol) had been added to the solution, the resulting mixture was stirred at room temperature overnight.…”

TRAM Linker: A Safety-Catch Linker for the Traceless Release of Acrylamides

“…Optimization of the cleavage sequence began with the final cleavage step. We used a volatile tertiary amine base (DIEA) along with an acid scavenger resin to allow the direct isolation of TRAM-derived acrylamides free from contaminating tertiary ammonium salts produced in the cleavage reaction. Four variables were considered: equivalents of DIEA, solvent, and both the identity and equivalents of the supported acid scavenger.…”