Asymmetric synthesis of (R)-hexane-1,5-diol and (R)-hex-3-ene-1,5-diol via a tandem asymmetric conjugate addition/stereospecific Meisenheimer rearrangement protocol

Tetrahedron Asymmetry

Volumn 7, Issue 4, 1996, Pages 1001-1004

  Davies, Stephen G ^a   Smyth, G Darren ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANEDIOL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029922498     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00102-4     Document Type: Article

References (24)

1. R.A.W. Johnstone, The Meisenheimer Rearrangement of Tertiary Amine Oxides, in Mechanism of Molecular Migrations, ed. B.S. Thyagarajan, Interscience, New York, 1969, Vol. 2, p. 249.
2. A. Albini, Synthesis, 1993, 263.
3. M. Moriwake, S. Sawada and Y. Inouye, J. Chem. Soc., Chem. Commun., 1970, 419; Y. Yamamoto, J. Oda and Y. Inouye, J. Chem. Soc., Chem. Commun., 1973, 848; M. Moriwaki, Y. Yamamoto, J. Oda and Y. Inouye, J. Org. Chem., 1976, 41, 300; Y. Yamamoto, J. Oda and Y. Inouye, J. Org. Chem., 1976, 41, 303.
4. M. Moriwake, S. Sawada and Y. Inouye, J. Chem. Soc., Chem. Commun., 1970, 419; Y. Yamamoto, J. Oda and Y. Inouye, J. Chem. Soc., Chem. Commun., 1973, 848; M. Moriwaki, Y. Yamamoto, J. Oda and Y. Inouye, J. Org. Chem., 1976, 41, 300; Y. Yamamoto, J. Oda and Y. Inouye, J. Org. Chem., 1976, 41, 303.
5. M. Moriwake, S. Sawada and Y. Inouye, J. Chem. Soc., Chem. Commun., 1970, 419; Y. Yamamoto, J. Oda and Y. Inouye, J. Chem. Soc., Chem. Commun., 1973, 848; M. Moriwaki, Y. Yamamoto, J. Oda and Y. Inouye, J. Org. Chem., 1976, 41, 300; Y. Yamamoto, J. Oda and Y. Inouye, J. Org. Chem., 1976, 41, 303.
6. M. Moriwake, S. Sawada and Y. Inouye, J. Chem. Soc., Chem. Commun., 1970, 419; Y. Yamamoto, J. Oda and Y. Inouye, J. Chem. Soc., Chem. Commun., 1973, 848; M. Moriwaki, Y. Yamamoto, J. Oda and Y. Inouye, J. Org. Chem., 1976, 41, 300; Y. Yamamoto, J. Oda and Y. Inouye, J. Org. Chem., 1976, 41, 303.
7. M.T. Reetz and E.H. Lauterbach, Tetrahedron Lett., 1991, 32, 4481.
8. R.W. Hoffmann, Angew. Chem., Int. Ed. Engl., 1979, 18, 563.
9. D. Enders and H. Kempen, Synlett, 1994, 969.
10. S.G. Davies and O. Ichihara, Tetrahedron: Asymmetry, 1991, 2, 183; S.G. Davies and D.R. Fenwick, J. Chem. Soc., Chem. Commun., 1995, 1109.
11. S.G. Davies and O. Ichihara, Tetrahedron: Asymmetry, 1991, 2, 183; S.G. Davies and D.R. Fenwick, J. Chem. Soc., Chem. Commun., 1995, 1109.
12. All new compounds gave satisfactory spectroscopic and microanalytical data.
13. J.C. Craig and K.K. Purushothaman, J. Org. Chem., 1970, 35, 1721.
14. M.A.T. Rogers, J. Chem. Soc., 1955, 769; J. Thesing and H. Mayer, Liebigs Ann. Chem., 1957, 609, 46; H. Stamm and J. Hoenicke, Arch. Pharm. (Weinheim), 1974, 307, 340; H.T. Nagasawa, J.G. Kohlhoff, P.S. Fraser and A.A. Mikhail, J. Med. Chem., 1972, 15, 483; N.A. LeBel and B.W. Caprathe, J. Org. Chem., 1985, 50, 3938.
15. M.A.T. Rogers, J. Chem. Soc., 1955, 769; J. Thesing and H. Mayer, Liebigs Ann. Chem., 1957, 609, 46; H. Stamm and J. Hoenicke, Arch. Pharm. (Weinheim), 1974, 307, 340; H.T. Nagasawa, J.G. Kohlhoff, P.S. Fraser and A.A. Mikhail, J. Med. Chem., 1972, 15, 483; N.A. LeBel and B.W. Caprathe, J. Org. Chem., 1985, 50, 3938.
16. M.A.T. Rogers, J. Chem. Soc., 1955, 769; J. Thesing and H. Mayer, Liebigs Ann. Chem., 1957, 609, 46; H. Stamm and J. Hoenicke, Arch. Pharm. (Weinheim), 1974, 307, 340; H.T. Nagasawa, J.G. Kohlhoff, P.S. Fraser and A.A. Mikhail, J. Med. Chem., 1972, 15, 483; N.A. LeBel and B.W. Caprathe, J. Org. Chem., 1985, 50, 3938.
17. M.A.T. Rogers, J. Chem. Soc., 1955, 769; J. Thesing and H. Mayer, Liebigs Ann. Chem., 1957, 609, 46; H. Stamm and J. Hoenicke, Arch. Pharm. (Weinheim), 1974, 307, 340; H.T. Nagasawa, J.G. Kohlhoff, P.S. Fraser and A.A. Mikhail, J. Med. Chem., 1972, 15, 483; N.A. LeBel and B.W. Caprathe, J. Org. Chem., 1985, 50, 3938.
18. M.A.T. Rogers, J. Chem. Soc., 1955, 769; J. Thesing and H. Mayer, Liebigs Ann. Chem., 1957, 609, 46; H. Stamm and J. Hoenicke, Arch. Pharm. (Weinheim), 1974, 307, 340; H.T. Nagasawa, J.G. Kohlhoff, P.S. Fraser and A.A. Mikhail, J. Med. Chem., 1972, 15, 483; N.A. LeBel and B.W. Caprathe, J. Org. Chem., 1985, 50, 3938.
19. C. Camiletti, D.D. Dhavale, L. Gentilucci and C. Trombini, J. Chem. Soc., Perkin Trans. I, 1993, 3157.
20. 3) 23.1 [C(6)], 35.3 [C(2)], 61.4 [C(1)], 68.5 [C(5)], 127.1 [C(3)], 137.0 [C(4)].
21. D. Parker and R.J. Taylor, Tetrahedron, 1987, 22, 5451.
22. 3) 21.8 [C(3)], 23.4 [C(6)], 32.3 and 38.7 [C(2) and C(4)], 62.3 [C(1)], 67.7 [C(5)].
23. K. Wada and T. Ishida, J. Chem. Soc., Perkin Trans. I, 1979, 1154.
24. N.C. Barua and R.R. Schmidt, Synthesis, 1986, 1067.