The highly enantiocontrolled functionalization of a 2-oxazolone heterocycle by intramolecular radical-based addition. A chiral synthon for 2- amino alcohols which contain three contiguous stereocenters

Tetrahedron Letters

Volumn 39, Issue 39, 1998, Pages 7131-7134

  Morita, Toru ^a   Matsunaga, Hirofumi ^a   Sugiyama, Eiji ^a   Ishizuka, Tadao ^a   Kunieda, Takehisa ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

Amino alcohols; Diastereoselection; Oxazolones; Radicals and radical reactions

Indexed keywords

2 OXAZOLONE DERIVATIVE; AMINOALCOHOL; HETEROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; CHLORINATION; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032563881     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01515-9     Document Type: Article

References (32)

1. 1. a) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org. Chem. 1988, 53, 3381-3383.
2. b) Ishizuka, T.; Ishibuchi, S.; Kunieda, T. Tetrahedron 1993, 49, 1841-1852.
3. c) Ishibuchi, S.; Ikematsu, Y.; Ishizuka, T.; Kunieda, T. Tetrahedron Lett. 1991, 32, 3523-3526.
4. d) Ishibuchi, S.; Nagatani, T.; Ishizuka, T.; Kunieda, T. Natural Products Lett. 1992, 1, 21-24.
5. 2. For recent papers, see: a) Hanessian, S.; Ninkovic, S. J. Org. CHem. 1996, 61, 5418-5424.
6. b) Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc. Perkin Trans, 1 1996, 793-802.
7. 3. For a review, see: Kunieda, T.; Ishizuka, T. J. Synth. Org. Chem., Jpn. 1997, 55, 1018-1027.
8. 4. Yamamoto, T.; Ishibuchi, S.; Ishizuka, T.; Haratake, M.; Kunieda, T. J. Org. Chem. 1993, 58, 1997-1998.
9. 5. a) Yoshioka, T.; Hara, T.; Takita, T.; Umezawa, H. J. Antibiot. 1974, 27, 356-357.
10. b) Ohgi, T.; Hecht, S. M. J. Org. Chem. 1981, 46, 1232-1234.
11. c) Narita, M.; Otsuka, M.; Kobayashi, S.; Ohno, M.; Umezawa, Y.; Morishima, H.; Saito, S.; Takita, T.; Umezawa, H. Tetrahedron Lett. 1982, 23, 525-528.
12. d) DiPardo, R. M.; Bock, M.G. ibid. 1983, 24, 4805-4808.
13. 6. a) Savignac, M.; Durand, J. O.; Genet, J. P. Tetrahedron: Asymmetry, 1994, 5, 717-722.
14. b) Tuch, A.; Saniere, M.; Merrer, Y. L.; Depezay, J. C. ibid. 1997, 8, 1649-6059.
15. 7. a) Kurosawa, N.; Ohfune, Y. J. Am. Chem. Soc. 1986, 108, 6041-6043.
16. b) Kurosawa, N.; Ohfune, Y. ibid. 1986, 108, 6043-6045.
17. 4, respectively, followed by treatment with DPPOx (Kunieda, T.; Abe, Y.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1981, 22, 1257-1260) as shown below. (Equation Presented)
18. 4, respectively, followed by treatment with DPPOx (Kunieda, T.; Abe, Y.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1981, 22, 1257-1260) as shown below. (Equation Presented)
19. 9. a) Matumoto, H.; Nikaido, T.; Nagai, Y. J. Org. Chem. 1976, 41, 396-398. (Equation Presented)
20. 4 Perfect regioselectivity might be rationalized primarily by the higher stability of the oxazolidin-4-yl radicals than the 5-yl radicals generated in situ.
21. 3).
22. 11. A differential NOE effect between Ha and Hb protons was observed.
23. 3SnH).
24. 1=H) ent-8b Data Centre. We are much indebted to the Yoshitomi Research Laboratories, Yoshitomi Pharmaceutical Ind. Ltd. (Fukuoka, Japan) for this X-ray crystallographic analysis.
25. 14. a) Matunaga, H.; Kimura, K.; Ishizuka, T.; Kunieda, T. Tetrahedron Lett. 1991, 32, 7751-7754.
26. b) Matunaga, H.; Ishizuka, T.; Marubayashi, N.; Kunieda, T. Chem. Pham. Bull. 1992, 40, 1077-1079.
27. 3).
28. 3).
29. 16. Shimizu, T.; Hiranuma, S.; Nakata, T. Tetrahedron Lett. 1996, 37, 6145-6148.
30. 17. a) Mitsunobu, O. Synthesis, 1981, 1-28.
31. b) Hughes, D. L. Org. React. 1992, 42, 335-656.
32. 18. Lipshutz, B. H.; Miller, T. A. Tetrahedron Lett. 1990, 31, 5253-5256.