Stereoselective preparation of functionalized tertiary P-chiral phosphine oxides by nucleophilic addition of lithiated tert-butylphenylphosphine oxide to carbonyl compounds

Tetrahedron Letters

Volumn 37, Issue 27, 1996, Pages 4729-4732

  Haynes, Richard K ^a   Lam, William W L ^a   Yeung, Lam Lung ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030199705     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00952-5     Document Type: Article

References (19)

1. 1. Hattacharya, A. K.; and Roy, N. K. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; John Wiley & Sons, 1992, p. 195; Valentine, D. in Asymmetric Synthesis, Vol. 4 "The Chiral Carbon Pool and Chiral Sulfur, Nitrogen, Phosphorus, and Silicon Centers" ed. J. D. Morrison and J. W. Scott; Academic Press 1984, Ch. 3.
2. 1. Hattacharya, A. K.; and Roy, N. K. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; John Wiley & Sons, 1992, p. 195; Valentine, D. in Asymmetric Synthesis, Vol. 4 "The Chiral Carbon Pool and Chiral Sulfur, Nitrogen, Phosphorus, and Silicon Centers" ed. J. D. Morrison and J. W. Scott; Academic Press 1984, Ch. 3.
3. 2. Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1300.
4. 3. Korpiun, O.; Mislow, K. J. Am. Chem. Soc. 1967, 89, 4784; Nudelman, A.; Cram, D. J. J. Am. Chem. Soc. 1968, 90, 3869; Lewis, R. A.; Mislow, K. J. Am. Chem. Soc. 1969, 91, 7009; Farnham, W. B.; Murray, R. K.; Mislow, K. J. Am. Chem. Soc. 1970, 92, 5809.
5. 3. Korpiun, O.; Mislow, K. J. Am. Chem. Soc. 1967, 89, 4784; Nudelman, A.; Cram, D. J. J. Am. Chem. Soc. 1968, 90, 3869; Lewis, R. A.; Mislow, K. J. Am. Chem. Soc. 1969, 91, 7009; Farnham, W. B.; Murray, R. K.; Mislow, K. J. Am. Chem. Soc. 1970, 92, 5809.
6. 3. Korpiun, O.; Mislow, K. J. Am. Chem. Soc. 1967, 89, 4784; Nudelman, A.; Cram, D. J. J. Am. Chem. Soc. 1968, 90, 3869; Lewis, R. A.; Mislow, K. J. Am. Chem. Soc. 1969, 91, 7009; Farnham, W. B.; Murray, R. K.; Mislow, K. J. Am. Chem. Soc. 1970, 92, 5809.
7. 3. Korpiun, O.; Mislow, K. J. Am. Chem. Soc. 1967, 89, 4784; Nudelman, A.; Cram, D. J. J. Am. Chem. Soc. 1968, 90, 3869; Lewis, R. A.; Mislow, K. J. Am. Chem. Soc. 1969, 91, 7009; Farnham, W. B.; Murray, R. K.; Mislow, K. J. Am. Chem. Soc. 1970, 92, 5809.
8. 4. Carey, J. V.; Barker, M. D.; Brown, J. M.; Russell, M. J. H. J. Chem. Soc., Perkin Trans. I, 1993, 831; Corey, E. J.; Chen, Z.-L. ; Tanoury, G. J. J. Am. Chem. Soc. 1993, 115, 11000.
9. 4. Carey, J. V.; Barker, M. D.; Brown, J. M.; Russell, M. J. H. J. Chem. Soc., Perkin Trans. I, 1993, 831; Corey, E. J.; Chen, Z.-L. ; Tanoury, G. J. J. Am. Chem. Soc. 1993, 115, 11000.
10. 5. Goodridge, R. G.; Hambley, T. W.; Haynes, R. K.; Ridley, D. D. J. Org. Chem., 1988, 53, 2881.
11. 6. Haynes, R. K.; Freeman, R. N.; Mitchell, C. R.; Vonwiller, S. C. J. Org. Chem. 1994, 59, 2919.
12. 7. Koeller, K. J.; Spilling, C. D. Tetrahedron Lett. 1991, 44, 6297; Kawashiwa, T.; Iwanaga, H.; Okazaki, R. Chem. Lett. 1993, 1531; Koeller, K. J.; Spilling, C. D. J. Org. Chem. 1995, 60, 931.
13. 7. Koeller, K. J.; Spilling, C. D. Tetrahedron Lett. 1991, 44, 6297; Kawashiwa, T.; Iwanaga, H.; Okazaki, R. Chem. Lett. 1993, 1531; Koeller, K. J.; Spilling, C. D. J. Org. Chem. 1995, 60, 931.
14. 7. Koeller, K. J.; Spilling, C. D. Tetrahedron Lett. 1991, 44, 6297; Kawashiwa, T.; Iwanaga, H.; Okazaki, R. Chem. Lett. 1993, 1531; Koeller, K. J.; Spilling, C. D. J. Org. Chem. 1995, 60, 931.
15. 8. Gordon, N. J.; Evans, S. A. J. Org. Chem. 1993, 58, 5293.
16. 9. All new compounds were characterized by spectroscopic methods and elemental analysis and/or accurate mass spectra.
17. 10. Harger, M. J. P. J. Chem. Soc., Perkin Trans. 2 1980, 1505.
18. 11. Full data are available from the authors.
19. 12. Eliel, E. L.; and Wilen, S. H., In Stereochemistry of Organic Compounds; John Wiley & Sons, 1994, Ch. 11.