000217887 001__ 217887
000217887 005__ 20180317092233.0
000217887 0247_ $$2doi$$a10.1021/acs.orglett.6b00483
000217887 022__ $$a1523-7052
000217887 02470 $$2ISI$$a000373519600032
000217887 037__ $$aARTICLE
000217887 245__ $$aSynthesis of Vinyl Isocyanides and Development of a Convertible Isonitrile
000217887 260__ $$aWashington$$bAmerican Chemical Society$$c2016
000217887 269__ $$a2016
000217887 300__ $$a4
000217887 336__ $$aJournal Articles
000217887 520__ $$aThe reaction of isocyanomethylenetriphenylphosphorane, generated in situ from the corresponding phosphonium salt, with a diverse set of aldehydes afforded vinyl isocyanides in good to high yields. Excellent E-selectivity was observed for aliphatic aldehydes and 2,6-disubstituted aromatic aldehydes, whereas Z-olefins were formed predominantly with ortho-substituted aryl aldehydes. (Z)-1-Bromo-2-(2-isocyanovinyl)benzene (5l) was found to be a truly universal isonitrile since, after Ugi reaction, the resulting secondary amide unit (RNHCO−) is convertible under both acidic and basic conditions. The application of 5l in the synthesis of polyheterocycles is also illustrated.
000217887 700__ $$aSpallarossa, Martina
000217887 700__ $$0244119$$aWang, Qian$$g205233
000217887 700__ $$aRiva, Renata
000217887 700__ $$0244710$$aZhu, Jieping$$g206332
000217887 773__ $$j18$$k7$$q1622-1625$$tOrganic Letters
000217887 909CO $$ooai:infoscience.tind.io:217887$$particle$$pSB
000217887 909C0 $$0252341$$pLSPN$$xU12326
000217887 917Z8 $$x206332
000217887 937__ $$aEPFL-ARTICLE-217887
000217887 973__ $$aEPFL$$rREVIEWED$$sPUBLISHED
000217887 980__ $$aARTICLE