Nitriles copper® trifluoromethanesulfonate

Decomposition of the diazoacetic ester (548) to the keto carbene (549) is promoted by copper(II) trifluoromethanesulfonate. In the presence of nitriles, 1,3-dipolar addition to the nitrile occurred giving the oxazole (550) (75JOM(88)ll5) (see also Section 4.03.8.1). [Pg.162]

Nagayoshi K. and Sato T. (1983) One-step synthesis of oxazoles from ketones and nitriles using copper(II) trifluoromethanesulfonate as a key reagent Chem Lett. 1355-1356. [Pg.373]

Prof. Hao s synthesis commenced with the copper(I) chloride-catalyzed oxidation of the tryptamine derivative to afford ketone 42 [74], A three-component Strecker-type reaction was designed to react the ketone 42 with tryptamine and TMSCN to finish the first ring closure. After examining a series of both Lewis acid and Bronsted acids, the authors found a catalytic amount of TMSOTf promoted the transformation and afforded nitrile intermediate 43, which is ready for the Houben-Hoesch-type cyclization [75]. Treatment by TfOH (trifluoromethanesulfonic acid) [76] in DCM and the... [Pg.516]

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