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Volumn 13, Issue 12, 1974, Pages 789-804

α‐Metalated Isocyanides in Organic Synthesis. New synthetic methods (6)

Author keywords

Isocyanides; Synthetic methods

Indexed keywords


EID: 84982385082     PISSN: 05700833     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.197407891     Document Type: Article
Times cited : (197)

References (189)
  • 7
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    • The chemistry of isocyanides has hitherto been limited largely to α‐addition of the isocyano group: review:, Academic Press, New york
    • (1971) Isonitrile Chemistry
    • Ugi, I.1
  • 16
  • 39
    • 84982380167 scopus 로고    scopus 로고
    • The bonding in organolithium compounds is complicated and varies according to the alkyl group and the solvent. For simplicity the lithiated isocyanides are here represented ionically in their structural formulas: cf., in [3 b], p.
    • Schöllkopf, U.1
  • 42
    • 84982374421 scopus 로고    scopus 로고
    • Dissertation, Universität Göttingen, planned for 1975.
    • Harms, R.1
  • 54
    • 84982348047 scopus 로고    scopus 로고
    • Dissertation, Universität Göttingen 1974.
    • Thoms, R.1
  • 75
    • 84982355275 scopus 로고    scopus 로고
    • Dissertation, Universität Göttingen 1973
    • Hantke, K.1
  • 79
    • 25544480497 scopus 로고
    • 1-Formylamino-1-arylsulfonyl-alkene aus α-metallierten Isocyanmethyl-arylsulfonen und Carbonylverbindungen; Umwandlung einer Carbonylverbindung in die nächsthöhere Carbonsäure
    • (1972) Angewandte Chemie , vol.84 , pp. 289
    • Schöllkopf, U.1    Schröder, R.2
  • 88
    • 84982367648 scopus 로고    scopus 로고
    • For conversion of isocyanides into formamides and for deformylation see [39] and literature cited therein.
  • 94
    • 84982376751 scopus 로고    scopus 로고
    • Dissertation, Universität Göttingen 1973.
    • Jentsch, S.1
  • 98
    • 84912380900 scopus 로고
    • The original isomers ratio can be shifted to ca. 3:1 in favor of cis‐(59a) by double lithiation and protonation:, Universität Göttingen
    • (1974) Diplomarbeit
    • Scheunemann, K.‐H.1
  • 110
    • 0001281349 scopus 로고
    • Neuere präparative Methoden der organischen Chemie II 13. Carbonyl-Olefinierung mit Triphenyl-phosphin-methylenen Wittig-Reaktion
    • also [3 b] and previous reviews cited therein
    • (1959) Angewandte Chemie , vol.71 , pp. 260
    • Schöllkopf, U.1
  • 111
    • 84982384810 scopus 로고
    • 2-Alkylthio-2-oxazolin-4-carbonsäureester und ihre Umwandlung in α-(N-Alkylthiocarbonyl-amino)acrylsäureester
    • For analogous ring openings see [36]; also
    • (1973) Angewandte Chemie , vol.85 , pp. 660
    • Hoppe, D.1
  • 113
    • 84982355299 scopus 로고    scopus 로고
    • Dissertation, Universität Göttingen 1969.
    • Markusch, P.1
  • 115
    • 84982359845 scopus 로고    scopus 로고
    • 71c was obtained only in the indicated configuration;, Berlin, personal communication.
    • Haffer, G.1
  • 132
    • 84982363507 scopus 로고    scopus 로고
    • For recognition of the relative configuration only one enantiomer is shown.
  • 148
  • 151
    • 84982380973 scopus 로고    scopus 로고
    • Dissertation, Universität Göttingen. 1974
    • Eilers, E.1
  • 154
    • 84982368552 scopus 로고    scopus 로고
    • Dehydration of diethyl formylaminomalonate also affords the 5‐alkoxy‐oxazole
    • Gerhart, F.1
  • 155
    • 84982358169 scopus 로고    scopus 로고
    • It is surprising that the esters 125 do not at least partially cyclize under the alkaline reaction conditions since ethyl α‐isocyanophenylacetate gives mainly 5‐ethoxy‐4‐phenyloxazole on distillation
    • Hoppe, D.1
  • 156
    • 84982381722 scopus 로고    scopus 로고
    • Dissertation, Universität Göttingen 1974.
    • Böhme, P.1
  • 173
    • 84982077638 scopus 로고
    • Synthesen mit α-metallierten Isocyaniden, XXV. 4-Cyan-2-isocyanalkansäure-äthylester, 4-Cyan-2-(formylamino)alkansäure-äthylester und 4-Cyan-5(4)-pyrrolin-2-carbonsäure-äthylester aus α-metallierten Isocyanalkansäure-äthylestern und Acrylnitrilen
    • (1973) Chemische Berichte , vol.106 , pp. 3382
    • Schöllkopf, U.1    Porsch, P‐H.2
  • 183
    • 33847805571 scopus 로고
    • As recently reported, (+)‐(S)‐l‐isocyano‐2,2‐diphenylcyclopropyllithium is configurationally stable below −50°C. It follows that mesomeric stabilization by the isocyano group plays no part: see:,. Notes added in proof (November 21, 1974)
    • (1974) J. Amer Chem. Soc. , vol.96 , pp. 3711
    • Walborsky, H.M.1    Periasamy, M.P.2
  • 184
    • 84982353104 scopus 로고    scopus 로고
    • very recently the first vinyl isocyanide 63 has been metalated: E/Z‐β‐styryl isocyanide 63a was lithiated with n‐butyllithium in tetrahydrofuran/ n‐pentane/diethyl ether (4:1:1) at −110°C (trapped by methyl iodide, trimethylchlorosilane, carbonyl compounds, and carbon dioxide)
  • 186
    • 84982351194 scopus 로고    scopus 로고
    • 2R in 71) on warming to 0°C in the presence of excess base. The reaction sequence with subsequent acid hydrolysis affords an “Eintopf” synthesis of 3‐ or 4‐pyridylalkyl (or aryl)ketones of type 76 in yields of 60 to 80


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