A metallocarbenoid approach to the formation of spirocyclic ammonium ylides leading to the preparation of medium-sized azacane rings

Tetrahedron Letters

Volumn 37, Issue 13, 1996, Pages 2165-2168

  Wright, Dennis L ^a   Weekly, R Matt ^a   Groff, Royce ^a   McMills, Mark C ^a  

^a OHIO UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; MORPHOLINE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029930972     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00221-3     Document Type: Article

References (22)

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2. b) Clark, J.S.; Hodgson, P.B. J. Chem. Soc., Chem. Commun. 1994, 2701-2.
3. Wright, D.L.; Weekly, R.M.; Groff, R.E.; McMills, M.C. 34th National Organic Symposium, Williamsburg, VA, June 1995, #232.
4. Sato, T.; Tsujimoto, K.; Matsubayashi, K.; Ishibashi, M.; Ikeda, M. Chem. Pharm. Bull. 1992, 40, 2308.
5. For the use of acyclic ylide rearrangements of vinyl pyrrolidine and piperidine to prepare similar azacycles see: a) Vedejs, E.; Hagen, J.P.; Roach, B.L.; Spear, K.L. J. Org. Chem., 1978, 43, 1185.
6. b) Vedejs, E.; Arco, M.J.; Powell, D.W.; Renga, J.M.; Singer, S.P. J. Org. Chem. 1978, 43, 4831.
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10. Regitz, M. Synthesis, 1972, 351.
11. For reports regarding the superiority of copper catalysts for generation of ammonium ylides see: a) West, F.G.; Naidu, B.N.; Tester, R.W. J. Org. Chem. 1994, 59, 6892.
12. b) ref. 1b. for generation of oxonium ylides see: Clark, J.S.; Krowiak, S.A.; Street, L.J. Tetrahedron Lett. 1993, 34, 4385.
13. Marko, I.E. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 913-73.
14. +), 180.
15. Enantiomeric excesses determined using Pirkle Type 1A, chiral phase HPLC with 95 : 5 hexane : isopropanol.
16. West, F.G.; Naidu, B.N. J. Am. Chem. Soc. 1994, 116, 8420.
17. +), 180.
18. For similar considerations see: West, F.G.; Naidu, B.N. J. Org. Chem. 1994, 59, 6057.
19. Giannis, A.; Kolter, T. I. Angew. Chem. Int. Ed. Engl., 1993, 32, 1244.
20. For a non-carbenoid based [2,3]-sigmatropic rearrangement of substituted vinyl aziridines see: a) Somfai, P.; Ahman, J. J. Am. Chem. Soc. 1994, 116, 9781.
21. b) Hassner, A.; Chau, W. Tetrahedron Lett. 1982, 23, 1989. For vinyl azetidines see: Hassner, A.; Wiegand, N. J. Org. Chem. 1986, 51, 3652.
22. b) Hassner, A.; Chau, W. Tetrahedron Lett. 1982, 23, 1989. For vinyl azetidines see: Hassner, A.; Wiegand, N. J. Org. Chem. 1986, 51, 3652.