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An array of organolithiums, magnesiates, enolates, and metalated nitriles add conjugately to \u03b2\u2010 and \u03b2,\u03b2\u2010disubstituted arylsulfonyl alkenyl isocyanides to rapidly assemble diverse isocyanide scaffolds. The intermediate metalated isocyanides are efficiently trapped with electrophiles to generate substituted isocyanides incorporating contiguous tri\u2010 and tetra\u2010substituted centers. The substituted isocyanides are ideally functionalized for elaboration into synthetic targets as illustrated by the three\u2010step synthesis of \u03b3\u2010carboline <jats:italic>N<\/jats:italic>\u2010methyl ingenine\u2005B.<\/jats:p>","DOI":"10.1002\/anie.201612574","type":"journal-article","created":{"date-parts":[[2017,3,14]],"date-time":"2017-03-14T16:01:25Z","timestamp":1489507285000},"page":"4310-4313","source":"Crossref","is-referenced-by-count":26,"title":["Alkenyl Isocyanide Conjugate Additions: A Rapid Route to \u03b3\u2010Carbolines"],"prefix":"10.1002","volume":"56","author":[{"given":"Sergiy V.","family":"Chepyshev","sequence":"first","affiliation":[{"name":"Department of Chemistry Drexel University  32 South 32nd St. Philadelphia PA 19104 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"J. 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Instituto Polit\u00e9cnico Nacional 2508 Ciudad de M\u00e9xico 07360 M\u00e9xico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Allen","family":"Chao","sequence":"additional","affiliation":[{"name":"Department of Chemistry Drexel University  32 South 32nd St. Philadelphia PA 19104 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9637-0246","authenticated-orcid":false,"given":"Fraser F.","family":"Fleming","sequence":"additional","affiliation":[{"name":"Department of Chemistry Drexel University  32 South 32nd St. Philadelphia PA 19104 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2017,3,13]]},"reference":[{"key":"e_1_2_2_1_1","first-page":"445","volume-title":"Science of Synthesis, Vol.\u200519","author":"Suginome M.","year":"2004"},{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2nj40050b"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201400017"},{"key":"e_1_2_2_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00083A"},{"key":"e_1_2_2_5_1","unstructured":"\u00a0"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527678174"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0505728"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200390167"},{"key":"e_1_2_2_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527652532"},{"key":"e_1_2_2_10_1","unstructured":"\u00a0"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.2174\/138955708786141007"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/b302359c"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-7091-6331-3_1"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/np9880500229"},{"key":"e_1_2_2_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527627097.ch13"},{"key":"e_1_2_2_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201107567"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201107567"},{"key":"e_1_2_2_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197506292"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19750871705"},{"key":"e_1_2_2_18_1","unstructured":"\u00a0"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1271\/bbb.57.659"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1271\/bbb1961.54.1845"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.197319730410"},{"key":"e_1_2_2_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/recl.19821010603"},{"key":"e_1_2_2_23_1","unstructured":"\u00a0"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0913307107"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200901587"},{"key":"e_1_2_2_25_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200901587"},{"key":"e_1_2_2_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr800309r"},{"key":"e_1_2_2_27_1","unstructured":"\u00a0"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr3002966"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200502220"},{"key":"e_1_2_2_29_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200502220"},{"key":"e_1_2_2_30_1","unstructured":"Some isocyanides are hydrolyzed during silica gel chromatography while others exhibit a pronounced tendency toward irreversible adsorption:"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-894X(98)00002-X"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)00562-0"},{"key":"e_1_2_2_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201403615"},{"key":"e_1_2_2_34_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200300590"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200300590"},{"key":"e_1_2_2_35_1","unstructured":"Two exceptions are vinyllithium (17\u2009% yield of the conjugate adduct) andtBuLi; 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