Chelation control in the ring opening and organometallic addition of α,β-epoxy aldehydes: A new entry to amino dihydroxyethylene dipeptide isostere subunits

European Journal of Organic Chemistry

Volumn , Issue 18, 2000, Pages 3127-3131

  Righi, Giuliana ^a   Chionne, Andrea ^a   Bonini, Carlo ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF BASILICATA   (Italy)

Author keywords

Aldehydes; Amino alcohols; Asymmetric synthesis; Grignard reactions

Indexed keywords

2 AMINO 1 CYCLOHEXYL 6 METHYLHEPTANE 3,4 DIOL; ALDEHYDE DERIVATIVE; ALPHA,BETA EPOXYALDEHYDE; AMINO DIHYDROXYETHYLENE DIPEPTIDE; BROMINE DERIVATIVE; DIPEPTIDE; HEPTANE; ORGANOMETALLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHELATION; CHEMICAL ANALYSIS; ISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033804339     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200009)2000:18<3127::AID-EJOC3127>3.0.CO;2-3     Document Type: Article

References (23)

1. For recent reviews, see: R. A. Johnson, K. B. Sharpless, Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH Publishers, Weinheim 1993, 103-158; T. Katsuki, V. S. Martin, Org. React. 1996, 1-300.
2. For recent reviews, see: R. A. Johnson, K. B. Sharpless, Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH Publishers, Weinheim 1993, 103-158; T. Katsuki, V. S. Martin, Org. React. 1996, 1-300.
3. [2a] Y. Liwschitz, Y. Rabinsohn, D. Perera, J. Chem. Soc. 1962, 1116-1119.
4. [2b] C. G. Caldwell, S. S. Bondy, Synthesis 1990, 34-36.
5. [2c] S. Saito, N. Takahashi, T. Ishikawa, T. Moriwake, Tetrahedron Lett. 1991, 32, 667-670.
6. see ref. 1 and: H. Hayakawa, N. Okada, M. Miyazawa, M. Miyashita, Tetrahedron Lett. 1999, 40, 4589-4592.
7. [4a] C. Bonini, G. Righi, G. Rumboldt, Tetrahedron 1995. 51, 13401-13407.
8. [4b] C. H. Beherens, K. B. Sharpless, J. Org. Chem. 1985, 50, 5696-5704.
9. [5a] For a review, see: C. Bonini, G. Righi, Symhesis 1994, 225-238.
10. [5b] C. Bonini, C. Federici, G. Righi, L. Rossi, J. Org. Chem. 1995, 60, 4803-4812.
11. [5c] C. Bonini, G. Righi, G. Rumboldt, J. Org. Chem. 1996, 61, 3557-3560
12. [5d] K. Otsubo, J. Inanaga, M. Yamaguchi, Tetrahedron Lett. 1987, 38, 4435-4438.
13. A. De Mico, R. Margarita, L. Parlanti, A. Vescovi, G. Piancatelli, J. Org. Chem. 1997, 62, 6974-6977.
14. S. Wang, G. P. Howe, R. S. Mahal, G. Procter, Tetrahedron Lett. 1992, 33, 3351.
15. [8a] B. M. Trost, I. Fleming, in Comprehensive Organic Synthesis, Pergamon Press, 1991, Vol. 1, Part 1.
16. [8b] W. C. Still, J. H. McDonald, Tetrahedron Lett. 1980, 21, 1031-1034.
17. C. Bonini, G. Righi, A. Chionne, R. D'Achille. Tetrahedron: Asymmetry 1997, 8, 903-906.
18. [10a] J. R. Luly, C.-N. Hsiao, N. BaMaung, J. J. Plattner, J. Org. Chem. 1988, 53, 6109-6112.
19. [10b] W. R. Baker, S. L. Condon, J. Org. Chem. 1993, 58, 3277.
20. [10c] D. J. Krysan, A. R. Haight, J. A. Menzia, N. Welch, Tetrahedron 1994, 50, 6163-6172.
21. [10d] C. W. Alexander, D. C. Liotta, Tetrahedron Lett. 1996, 37, 1961-1964.
22. [10e] M. Haddad, M. Larcheveque, Tetrahedron Lett. 1996, 37, 4525-4528.
23. [10f] S. Chadrasekhar, S. Mohapatra, J. S. Yadav, Tetrahedron 1999, 55, 4763-4768.