An unusual tandem cyclization-Stevens rearrangement mediated by Ph3P/DEAD or Bu3P/ADDP

Tetrahedron Letters

Volumn 37, Issue 45, 1996, Pages 8133-8136

  Walker, Michael A ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIDINE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030569263     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01891-6     Document Type: Article

References (27)

1. 1. Abbreviations: ADDP; 1,1′-(azodicarbonyl)dipiperidine, DEAD; diethyl azodicarboxylate.
2. 2. Recent review; Hughes, D. L. Org. Prep. Proc. Intl. 1996, 28, 129
3. 3. See references cited in ref 2
4. 4. Wojciechowska, H.; Pawlowicz, R.; Andruszkiewicz, R.; Grzybowska Tetrahedron Lett. 1978, 42, 4063. Comins, D. L.; Jianhua, G. Tetrahedron Lett. 1994, 35, 2819. Charette, A. B.; Coté, B.; Moroc, S.; Prescott, S. J. Org. Chem. 1995, 60, 6888.
5. 4. Wojciechowska, H.; Pawlowicz, R.; Andruszkiewicz, R.; Grzybowska Tetrahedron Lett. 1978, 42, 4063. Comins, D. L.; Jianhua, G. Tetrahedron Lett. 1994, 35, 2819. Charette, A. B.; Coté, B.; Moroc, S.; Prescott, S. J. Org. Chem. 1995, 60, 6888.
6. 4. Wojciechowska, H.; Pawlowicz, R.; Andruszkiewicz, R.; Grzybowska Tetrahedron Lett. 1978, 42, 4063. Comins, D. L.; Jianhua, G. Tetrahedron Lett. 1994, 35, 2819. Charette, A. B.; Coté, B.; Moroc, S.; Prescott, S. J. Org. Chem. 1995, 60, 6888.
7. 5. Hedaya, E.; Theodoropulus, S. Tetrahedron 1968, 24, 2241. Bittner, S.; Assaf, Y.; Krief, P.; Pomerantz, M.; Ziemnicka, B. T.; Smith, G. S. J. Org. Chem. 1985, 50, 1712. Castro, J. L.; Matassa, V. G.; Ball, R. G. J. Org. Chem. 1994, 59, 2289.
8. 5. Hedaya, E.; Theodoropulus, S. Tetrahedron 1968, 24, 2241. Bittner, S.; Assaf, Y.; Krief, P.; Pomerantz, M.; Ziemnicka, B. T.; Smith, G. S. J. Org. Chem. 1985, 50, 1712. Castro, J. L.; Matassa, V. G.; Ball, R. G. J. Org. Chem. 1994, 59, 2289.
9. 5. Hedaya, E.; Theodoropulus, S. Tetrahedron 1968, 24, 2241. Bittner, S.; Assaf, Y.; Krief, P.; Pomerantz, M.; Ziemnicka, B. T.; Smith, G. S. J. Org. Chem. 1985, 50, 1712. Castro, J. L.; Matassa, V. G.; Ball, R. G. J. Org. Chem. 1994, 59, 2289.
10. 3, DMF).
11. 7. Walker, M. A. J. Org. Chem. 1995, 60, 5352.
12. 8. Intramolecular cyclization of dialkyl amino groups to form quaternary ammoinum salts has been observed (or implied by product stereochemistry) previously under Mitsunobu conditions. Dow, R. L.; Kelly, R. C.; Schletter, I.; Wierenga, W.Syn. Comm. 1981, 11, 43. Freedman, J.; Vaal, M. J.; Huber, E. W. J. Org. Chem. 1991, 56, 670.
13. 8. Intramolecular cyclization of dialkyl amino groups to form quaternary ammoinum salts has been observed (or implied by product stereochemistry) previously under Mitsunobu conditions. Dow, R. L.; Kelly, R. C.; Schletter, I.; Wierenga, W.Syn. Comm. 1981, 11, 43. Freedman, J.; Vaal, M. J.; Huber, E. W. J. Org. Chem. 1991, 56, 670.
14. 9. Yamada, T.; Manabe, Y.; Miyazawa, T.; Kuwata, S.; Sera, A. J. Chem. Soc. Chem. Comm. 1984, 1500. Tempé, J. in, "Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins, Vol. 7" Boris Weinstein Ed., Marcel Dekker, New York, 1983.
15. 9. Yamada, T.; Manabe, Y.; Miyazawa, T.; Kuwata, S.; Sera, A. J. Chem. Soc. Chem. Comm. 1984, 1500. Tempé, J. in, "Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins, Vol. 7" Boris Weinstein Ed., Marcel Dekker, New York, 1983.
16. N2 step of the Mitsunobu reaction is only weakly dependent on nucleophile basicity. Hughes, D. L.; Reamer, R. A.; Bergan, J. J.; Grabowski, E. J. J. J. Am. Chem. Soc. 1988, 110, 6487.
17. 11. Pine, S. H. Org. React. 1970, 18, 403.
18. 3, which may be the actual activated intermediate under these conditions rather than alkoxyphosphonium salt 6. Guthrie, R. D.; Jenkins, I. D. Aust. J. Chem. 1982, 35, 767. von Itzstein, M.; Jenkins, I. D. ibid 1983, 36, 557. Idem J. Chem. Soc., Perkin Trans I, 1986, 437. Grochowski, E.; Hilton, B. D.; Kupper, R. J.; Michejda, C. J.; J. Am. Chem. Soc. 1982, 104, 6876.
19. 3, which may be the actual activated intermediate under these conditions rather than alkoxyphosphonium salt 6. Guthrie, R. D.; Jenkins, I. D. Aust. J. Chem. 1982, 35, 767. von Itzstein, M.; Jenkins, I. D. ibid 1983, 36, 557. Idem J. Chem. Soc., Perkin Trans I, 1986, 437. Grochowski, E.; Hilton, B. D.; Kupper, R. J.; Michejda, C. J.; J. Am. Chem. Soc. 1982, 104, 6876.
20. 3, which may be the actual activated intermediate under these conditions rather than alkoxyphosphonium salt 6. Guthrie, R. D.; Jenkins, I. D. Aust. J. Chem. 1982, 35, 767. von Itzstein, M.; Jenkins, I. D. ibid 1983, 36, 557. Idem J. Chem. Soc., Perkin Trans I, 1986, 437. Grochowski, E.; Hilton, B. D.; Kupper, R. J.; Michejda, C. J.; J. Am. Chem. Soc. 1982, 104, 6876.
21. 3, which may be the actual activated intermediate under these conditions rather than alkoxyphosphonium salt 6. Guthrie, R. D.; Jenkins, I. D. Aust. J. Chem. 1982, 35, 767. von Itzstein, M.; Jenkins, I. D. ibid 1983, 36, 557. Idem J. Chem. Soc., Perkin Trans I, 1986, 437. Grochowski, E.; Hilton, B. D.; Kupper, R. J.; Michejda, C. J.; J. Am. Chem. Soc. 1982, 104, 6876.
22. 4; (MH+) 300.2. Found; 300.4
23. +). Found: 314.2.
24. 15. Based on the relative rates for cyclization of: 5>6>3>4. Carey, F. A.; Sundberg, R. J.; "Advanced Organic Chemistry, Part A: Structure and Mechanism" Plenum Press, New York, 1990.
25. 16. Aziridination of amino-ethanol analogs under standard Mitsunobu conditions is difficult and is reported to result in by-products such as 11a especially if the tether linking the amino and hydroxyl groups is unsubstituted. Pfister, J. R.; Synthesis 1984, 969.
26. 17. Marko, I. E. in "Comprehensive Organic Synthesis, Vol 3", Pattenden, G. Ed.; Pergammon Press, New York, 1991. Pine, S. H. Org. React., 1970, 18, 403.
27. 17. Marko, I. E. in "Comprehensive Organic Synthesis, Vol 3", Pattenden, G. Ed.; Pergammon Press, New York, 1991. Pine, S. H. Org. React., 1970, 18, 403.