Synthesis of New Ferrocenyl‐Substituted Aziridines via the Gabriel–Cromwell Reaction

References

• Garner , P. , Dogan , Ö. , Youngs , W. J. , Kennedy , V. O. , Protasiewicz , J. and Zaniewski , R. 2001 . Stereocontrolled 1,3‐dipolar cycloadditions using oppolzer's camphor sultam as the chiral auxiliary for carbonyl stabilized azomethine ylides . Tetrahedron , 57 : 71
   Google Scholar
• Bonini , B. F. , Fochi , M. , Comes‐Franchini , M. , Ricci , A. , Thijs , L. and Zwanenburg , B. 2003 . Synthesis of ferrocenyl‐oxazolines by ring expansion of N‐ferrocenoyl‐aziridine‐2‐carboxylic esters . Tetrahedron: Asymmetry , 14 : 3321
   Google Scholar
• Davis , F. A. , Reddy , G. V. and Liu , H. 1995 . Asymmetric synthesis of 2H‐azirines: First enantioselective synthesis of the cytotoxic antibiotic (R)‐(−)‐dysidazirine . J. Am. Chem. Soc. , 117 : 3651
   Web of Science ®Google Scholar
• Spears , G. W. , Naganishi , K. and Ohfune , Y. 1991 . Novel Entry to a 3,4‐disubstituted 2‐azetidinone derivative via palladium‐assisted carbonylation of a 2‐substituted 3‐vinylaziridine . Synlett , : 91
   Google Scholar
• Ahman , J. and Somfai , P. 1995 . Enantiselective total synthesis of (−)‐indolizidines 209 band 209D via a highly efficient aza‐[2,3]‐wittig rearrangement of vinylaziridines . Tetrahedron , 51 : 9747
   Google Scholar
• Pearson , W. H. 1985 . Synthesis of fused pyrrolines by the intramolecular cycloadition of azides application to the pyrrolizidine alkaloids . Tetrahedron Lett. , 26 : 3527
   Google Scholar
• Carreaux , F. , Dureault , A. and Depezay , J. C. 1992 . Tartaric acid derived aziridines as chiral precursors of 3‐amino‐3‐deoxy and 2‐amino‐2‐deoxy tetroses: An efficient approach towards mugineic acid . Synlett , : 527
   Google Scholar
• Kasai , M. and Kono , M. 1992 . Studies on the chemistry of mitomycins . Synlett , : 778
   Google Scholar
• Katoh , T. , Itoh , E. , Yoshino , T. and Terashima , S. 1997 . Total synthesis of an enantiomeric pair of FR900482:1, Synthetic and end‐game strategies . Tetrahedron , 53 : 10229
   Google Scholar
• Skibo , E. B. , Islam , I. , Heileman , M. J. and Schulz , W. G. 1994 . Structure‐activity studies of benzimidazole‐based DNA‐cleaving agents: Comparison of benzimidazole, pyrrolobenzimidazole, and tetrahydropyridobenzimidazole analogs . J. Med. Chem. , 37 : 78
   PubMed Web of Science ®Google Scholar
• Wang , M.‐C. , Wang , D.‐K. , Zhu , Y. , Liu , L.‐T. and Guo , Y.‐F. 2004 . Enantiopure N‐ferrocenylmethylaziridin‐2‐ylmethanols from L‐serine: synthesis, crystal structure and application . Tetrahedron: Asymmetry , 15 : 1289
   Google Scholar
• Sweeney , J. B. 2002 . Aziridines: Epoxides' ugly cousins? . Chem. Soc. Rev. , 31 : 247 For reviews concerning the synthesis of aziridines, see (a)
   PubMed Web of Science ®Google Scholar
• Osborn , H. M.I. and Sweeney , J. 1997 . The asymmetric synthesis of aziridines . Tetrahedron: Asymmetry , 8 : 1693
   Web of Science ®Google Scholar
• Kemp , J. E. G. 1991 . Comprehensive Organic Synthesis Edited by: Trost , B. M. and Fleming , I. Vol. 7 , 467 Oxford : Pergamon .
   Google Scholar
• Padwa , A. and Murphree , S. S. 2000 . Progress in Heterocyclic Chemistry Edited by: Gribble , G. W. and Gilchrist , T. L. Vol. 12 , 57 Oxford : Pergamon Elsevier Science . Chapter 4.1
   Google Scholar
• Tanner , D. 1994 . Chiral aziridines—their synthesis and use in stereoselective transformations . Angew. Chem. Int. Ed. Engl. , 33 : 599
   Web of Science ®Google Scholar
• McCoull , W. and Davis , F. A. 2000 . Recent synthetic applications of chiral aziridines . Synthesis , : 1347
   Google Scholar
• Garner , P. P. , Dogan , Ö. and Pillai , S. 1994 . Auxiliary mediated synthesis of aziridine‐2‐carboxylic acid derivatives . Tetrahedron Lett. , 35 : 1653
   Web of Science ®Google Scholar
• Dogan , Ö. and Garner , P. P. 2000 . Auxiliary controlled intramolecular 1,3‐dipolar cycloaddition reactions of chiral azomethine ylides . Turk. J. Chem. , 24 : 59
   Google Scholar
• Howorth , J. and Hanlon , K. 2001 . Novel N‐ferrocenylmethyl, N′‐methyl‐2‐substituted benzimidazolium iodide salts with in vitro activity against the P. falciparum malarial parasite strain NF54 . Tetrahedron Lett. , 42 : 751
   Web of Science ®Google Scholar
• Abran , A. , Csampai , A. , Böcskei , Z. and Sohair , P. 1999 . Study on ferrocenes, part 6: 1,3‐dipolar cycloadditions of heterocyclic hydrazones of formylferrocene . Tetrahedron , 55 : 5441
   Web of Science ®Google Scholar
• Köpf‐Maier , P. , Köpf , H. and Neuse , E. W. 1984 . Ferricenium complexes—A new type of water‐soluble antitumor agent . Cancer Res. Clin. Oncol. , 108 : 336
   PubMed Web of Science ®Google Scholar
• Patti , A. and Nicolosi , G. 2000 . Preparation of chiral C 2‐symmetrical 1,1′‐disubstituted ferrocenes . Tetrahedron: Asymmetry , 11 : 3687 and references cited therein
   Google Scholar
• Fukuda , T. , Takehara , A. , Haniu , N. and Iwao , M. 2000 . Synthesis of chiral primary 1‐ferrocenylalkylamines via highly diastereoselective addition of organolithium compounds to ferrocenecarboxaldehyde imine derived from (S)‐2‐methoxy‐1‐phenylethylamine . Tetrahedron: Asymmetry , 11 : 4083
   Google Scholar
• Grevels , F.‐W. , Kuran , A. , Özkar , S. and Zora , M. 1999 . Friedel–Crafts alkylation of ferrocene with Z‐cyclooctene and cyclohexene . J. Organomet. Chem. , 587 : 122
   Web of Science ®Google Scholar
• Hayashi , T. and Togni , A. 1995 . Ferrocenes Edited by: Hayashi , T. and Togni , A. Weinheim : VCH .
   Google Scholar
• Dogan , Ö. , Şenol , V. , Zeytinci , S. , Koyuncu , H. and Bulut , A. 2005 . Efficient synthesis of ferrocenylenones by Friedel‐Crafts acylation with EtAlCl2‐Me3Al . J. Organomet. Chem. , 690 : 430
   Web of Science ®Google Scholar
• Liu , W. , Xie , T. , Liang , Y. , Liu , W. and Ma , Y. 2001 . Bromination of ferrocene chalcone derivatives mediated by β‐cyclodextrin . J. Organomet. Chem. , 627 : 93 Because of the difficulty in direct bromination, ferrocenyl chalcone derivatives were brominated by forming inclusion complex with cyclodextrin. See
   Google Scholar
• Nagel , D. L. , Woller , P. B. and Cromwell , N. H. 1971 . Nuclear magnetic resonance spectra and nitrogen inversion in 1‐alkyl‐2‐aryl‐3‐carboaziridines . J. Org. Chem. , 36 : 3911
   Google Scholar
• Amal Raj , A. and Raghunathan , R. 2003 . Synthesis of spiro pyrrolidines via formal [3+2] cycloaddition of unusual enones and cis‐3‐benzoyl‐1‐cyclohexyl‐2‐phenylaziridine . Tetrahedron , 59 : 2907
   Google Scholar
• Tanner , D. and Somfai , P. 1993 . Palladium‐catalyzed transformation of a chiral vinylaziridine to a β‐lactam: An enantioselective route to the carbapenem (+)‐PS‐5 . Bioorg. Med. Chem. Lett. , 3 : 2415
   Google Scholar
• Cantrill , A. A. , Osborn , H. M.I. and Sweeney , J. 1998 . Preparation and ring‐opening reactions of N‐diphenylphosphinyl aziridines . Tetrahedron , 54 : 2181
   Google Scholar
• Satoh , T. and Fukuda , Y. 2003 . A new synthesis of enantiomerically pure α‐ and β‐amino acid derivatives using aziridinyl anions . Tetrahedron , 59 : 9803
   Google Scholar
• Baldwin , J. E. , Adlington , R. M. and Robinson , N. G. 1987 . Nucleophilic ring opening of aziridine‐2‐carboxylates with Wittig reagents; an enantioefficient synthesis of unsaturated amino acids . J. Chem. Soc. Chem. Commun. , : 153
   Google Scholar
• Sato , K. and Koziskowski , A. P. 1989 . Construction of optically pure tryptophans from serine derived aziridine‐2‐carboxylates . Tetrahedron Lett. , 30 : 4073
   Web of Science ®Google Scholar
• Church , N. J. and Young , D. W. 1995 . Synthesis of α‐amino acids by ring opening of aziridine‐2‐carboxylates with carbon nucleophiles . Tetrahedron Lett. , 36 : 151
   Web of Science ®Google Scholar