Organolithium-induced alkylative ring opening of aziridines: Synthesis of unsaturated amino alcohols and ethers

Journal of Organic Chemistry

Volumn 71, Issue 22, 2006, Pages 8510-8515

  Hodgson, David M ^a   Štefane, Bogdan ^a   Miles, Timothy J ^a   Witherington, Jason ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ETHERS; LITHIUM COMPOUNDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

AMINO ALCOHOLS; DESYMMETRIZATION; ENANTIOMERS; ORGANOLITHIUMS;

AMINES;

1,4 DIMETHOXYBUT 2 ENE; ALKYL GROUP; AMINOALCOHOL; AZIRIDINE; AZIRIDINE DERIVATIVE; AZIRIDINYL ETHER; BUTANE; ETHER; ETHER DERIVATIVE; METHYL GROUP; ORGANOLITHIUM COMPOUND; UNCLASSIFIED DRUG;

ALCOHOL PRODUCTION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL REACTION; CIS ISOMER; ENANTIOMER; ENANTIOSELECTIVITY; NONHUMAN; RING OPENING; TRANS ISOMER;

ALKYLATION; AMINO ALCOHOLS; AZIRIDINES; ETHERS; LITHIUM; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 33750464104     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0615201     Document Type: Article

References (52)

1. (a) Rubottom, G. M.; Stevenson, G. R.; Chabala, J. C.; Pascucci, V. L. Tetrahedron Lett. 1972, 3591-3594.
2. For recent reviews on aziridinyl and oxiranyl anions, see: (b) Oxiranyl and aziridinyl anions as reactive intermediates in synthetic organic chemistry. Florio, S., Ed.; Tetrahedron 2003, 59, 9683-9864.
3. (c) Hodgson, D. M.; Bray, C. D. In Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: Weinheim, 2006; pp 145-184.
4. (d) Hodgson, D. M.; Bray, C. D.; Humphreys, P. G. Synlett. 2006, 1-22.
5. Boche, G.; Lohrenz, J. C. W. Chem. Rev. 2001, 101, 697-756.
6. (a) Beak, P.; Wu, S.; Yum, E. K.; Jun, Y. M. J. Org. Chem. 1994, 59, 276-277.
7. (b) Hodgson, D. M.; Humphreys, P. G.; Ward, J. G. Org. Lett. 2005, 7, 1153-1156.
8. (a) Arjona, O.; Menchaca, R.; Plumet, J. Heterocycles 2001, 55, 5-7.
9. (b) Müller P.; Nury, P. Helv. Chim. Acta 2001, 84, 662-677.
10. (c) O'Brien, P.; Rosser, C. M.; Caine, D. Tetrahedron 2003, 59, 9779-9791.
11. (d) Müller, P.; Riegert, D.; Bernardinelli, G. Helv. Chim. Acta 2004, 87, 227-239.
12. Hodgson, D. M.; Miles, S. M. Angew. Chem., Int. Ed. 2006, 45, 935-938.
13. Hodgson, D. M.; Humphreys, P. G.; Ward, J. G. Org. Lett. 2006, 8, 995-998.
14. (a) Crandall, J. K.; Lin, L.-H. C. J. Am. Chem. Soc. 1967, 89, 4527-4528.
15. (b) Doris, E.; Dechoux, L.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 7943-7946.
16. (c) Hodgson, D. M.; Fleming, M. J.; Stanway, S. J. J. Am. Chem. Soc. 2004, 126, 12250-12251.
17. (a) Dechoux, L.; Doris, E.; Mioskowski, C. Chem. Commun. 1996, 549-550.
18. (b) Doris, E.; Dechoux, L.; Mioskowski, C. Synlett 1998, 337-343.
19. (a) Hodgson, D. M.; Stent, M. A. H.; Wilson, F. X. Org. Lett. 2001, 3, 3401-3403.
20. (b) Hodgson, D. M.; Miles, T. J.; Witherington, J. Synlett 2002, 310-312.
21. (c) Hodgson, D. M.; Stent, M. A. H.; Wilson, F. X. Synthesis 2002, 1445-1453.
22. (d) Hodgson D. M.; Maxwell, C. R.; Miles, T. J.; Paruch, E.; Stent, M. A. H.; Matthews, I. R.; Wilson, F. X.; Witherington, J. Angew. Chem., Int. Ed. 2002, 41, 4313-4316.
23. (e) Hodgson D. M.; Stent M. A. H.; Štefane B.; Wilson F. X. Org. Biomol. Chem. 2003, 1, 1139-1150.
24. (f) Hodgson, D. M.; Miles, T. J.; Witherington, J. Tetrahedron 2003, 59, 9729-9742.
25. (g) Hodgson, D. M.; Maxwell, C. R.; Miles, T. J.; Paruch, E.; Matthews, I. R.; Witherington, J. Tetrahedron 2004, 60, 3611-3624.
26. (a) Kunieda, T.; Ishizuka, T. In Studies in Natural Products Chemistry; Rahman, A., Ed.; Elsevier: Amsterdam, 1993; Vol. 12, pp 411-445.
27. (b) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875.
28. (c) Bergmeier, S. C. Tetrahedron 2000, 56, 2561-2576.
29. Flock, S.; Frauenrath, H. Synlett 2001, 839-841.
30. Hodgson, D. M.; Štefane, B.; Miles, T. J.; Witherington, J. Chem. Commun. 2004, 2234-2235.
31. Rosser, C. M.; Coote, S. C.; Kirby, J. P.; O'Brien, P.; Caine, D. Org. Lett. 2004, 6, 4817-4819.
32. Sun, P.; Weinreb, S. M.; Shang, M. Y. J. Org. Chem. 1997, 62, 8604-8608.
33. Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844-6845.
34. Barili, P. L.; Berti, G.; Mastrorilli, E. Tetrahedron 1993, 49, 6263-6265.
35. Reppe, W. Liebigs Ann. Chem. 1955, 596, 1-224.
36. Smith, P. W.; Whittington, A. R.; Cobley, K. N.; Jaxa-Chamiec, A.; Finch, H. J. Chem. Soc., Perkin Trans. 1 2001, 21-25.
37. No improvement in yield was observed using TsNBrNa (Chanda, B. M.; Vyas, R.; Bedekar, A. V. J. Org. Chem. 2001, 66, 30-34) instead of TsNClNa.
38. Fuji, K.; Kawabata, T.; Kiryu, Y.; Sugiura, Y.; Taga, T.; Miwa, Y. Tetrahedron Lett. 1990, 31, 6663-6666.
39. Gontcharov, A. V.; Liu, H.; Sharpless, K. B. Org. Lett. 1999, 1, 783-786.
40. Huang, J.; O'Brien, P. Synthesis 2006, 425-434.
41. Fleming, I.; Dunoguès, J.; Smithers, R. Org. React. 1989, 37, 57-575.
42. Ager, D. J. Org. React. 1990, 38, 1-223.
43. Kasatkin, A. N.; Whitby, R. J. Tetrahedron Lett. 2000, 41, 5275-5280.
44. For a review, see: Topics in Organometallic Chemistry: Organolithiums in Enantioselective Synthesis: Hodgson, D. M., Ed.; Springer: Heidelberg, 2003 Vol. 5.
45. Huang, J. O'Brien, P. Chem. Commun. 2005, 5696-5697.
46. Ohno, H.; Hamaguchi, H.; Ohata, M.; Kosaka, S.; Tanaka, T. J. Am. Chem. Soc. 2004, 126, 8744-8754.
47. See Supporting Information for details.
48. (a) Seebach, D.; Kalinowski, H.-O.; Bastani, B.; Crass, G.; Daum, H.; Doerr, H.; DuPreez, N. P.; Ehrig, V.; Langer, W.; Nussler, C.; Oei, H.-A.; Schmidt, M. Helv. Chim. Acta 1977, 60, 301-325.
49. (b) Mash, E. A.; Nelson, K. A.; Van Deusen, S.; Hemperly, S. B. Organic Syntheses; Wiley: New York, 1993; Collect. Vol. VIII. pp 155-158.
50. (c) Hoshino, J.; Hiraoka, J.; Hata, Y.; Sawada, S.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1995, 693-697.
51. (d) Shi, M.; Jiang, J.-K.; Feng, Y.-S. Tetrahedron: Asymmetry 2000, 11, 4923-4933.
52. Lohray, B. B.; Gao Y.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 2623-2626.