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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 30, 2000 - Issue 17
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Original Articles

Tert-Butyldiphenylsilylmethyl Triflate: Preparation and Dipolar Cycloaddition Reactions of 1-(Tert-Butyldiphenylsilylmethyl)-6-Cyano-4-Methyl-1,2,5,6-Tetrahydropyridine

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Pages 3203-3213 | Received 05 Dec 1999, Published online: 04 Dec 2007

References

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  • Fry , E. M. and Beisler , J. A. 1970 . J. Org. Chem. , 35 : 2809
  • Guerrier , L. , Royer , J. , Grierson , D. S. and Husson , H.-P. 1983 . J. Am. Chem. Soc. , 105 : 7754
  • Bosch , J. , Rubiralta , M. and Bolos , J. 1987 . Tetrahedron , 43 : 391
  • 1998 . The Ohio State University . This paper is abstracted in part from the Ph.D. Thesis of Y. Huang
  • Terao , Y. , Aono , M. and Achiwa , K. 1988 . Heterocycles , 27 : 981
  • Vedejs , E. and West , F. 1988 . Chem. Rev. , : 941 For reviews of azomethine ylid cycloadditions see:
  • Padwa , A. and Chen , Y.-Y. 1983 . Tetrahedron Lett. , 24 : 3447
  • Parker , K. A. , Cohen , I. D. , Padwa , A. and Dent , W. 1984 . Tetrahedron Lett. , 25 : 4917
  • Padwa , A. , Chen , Y.-Y. , Dent , W. and Nimmesgern , H. 1985 . J. Org. Chem. , 50 : 4006
  • Terao , Y. , Kotaki , H. , Imai , N. and Achiwa , K. 1985 . Chem. Pharm. Bull. , 33 : 896
  • Imai , N. , Terao , Y. , Achiwa , K. and Sekiya , M. 1984 . Tetrahedron Lett. , 25 : 1579 For related entries to azomethine ylids see
  • Hosomi , A. , Sakata , Y. and Sakurai , H. 1984 . Chem. Lett. , : 1117
  • Terao , Y. , Kotaki , H. , Imai , N. and Achiwa , K. 1985 . Chem. Pharm. Bull. , 33 : 2762
  • Vedejs , E. and Martinez , G. R. 1980 . J. Am. Chem. Soc. , 102 : 7993
  • Cuadrado , P. , Gonzalez , A. M. , Ganzalez , B. and Pulido , F. J. 1989 . Synth. Commun. , 19 : 275
  • It is notable that reaction of 11 with liquid ammonia in tetrahydrofuran provides Ph2 t -BuSiCH2NH2 as a pale yellow oil in 97% yield: IR (neat) 3372 cm-1 1H NMR (CDCl3, 300 MHz) δ 0.98 (s, 2H), 1.16 (s, 9H), 2.89 (s, 2H), 7.36-7.42 (m, 6H), 7.68-7.75 (m, 4H); 13C NMR (CDCl3, 75.47 MHz) δ 18.0 (s), 25.4 (t), 27.8 (q), 127.8 (d), 129.3 (d), 133.1 (s), 135.9 (d); exact mass calcd for C17H23,NSi m/e 269.1600, found m/e 269.1591. This compound has been found to participate as a nucleophile in alkylation reactions with alkyl halides, N-acylation reactions with lactones, and imine-forming reactions with aldehydes (Strecker synthesis). Details are elaborated in the thesis cited in reference 3.
  • Bosch , J. , Feliz , M. and Bennasar , M.-L. 1984 . Tetrahedron , 40 : 1419
  • Rubiralta , M. , Diez , A. and Bosch , J. 1988 . Heterocycles , 27 : 785
  • The pyridines used to prepare 15 and 17 were synthesized by treatment of 3-acetylpyridine with methyllithium and sodium borohydride, respectively
  • Treatment of 12 with silver fluoride in the presence of trans-1,2-bis(phenyl-sulfonyl)ethylene also provided a 20% yield of a 1:1 mixture of diastereomeric cycloadducts derived from ylid 25. Less reactive dipolarophiles failed to give cycloadducts
  • Procedures are provided for representative reactions and less detail for related reactions
  • Antonsen , O. , Benneche , T. and Undheim , K. 1992 . Acta Chim. Scand. , 46 : 757 Alcohol 10 has been reported only as a minor product during the course of unrelated studies

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