Unprecedented base effect on the synthesis of chiral phosphinate esters: A new route to P-chiral phosphine oxides of high enantiomeric purity

Tetrahedron Asymmetry

Volumn 7, Issue 12, 1996, Pages 3353-3356

  Benabra, Abdelhak ^b   Alcudia, Ana ^b   Khiar, Noureddine ^a   Fernández, Inmaculada ^b   Alcudia, Felipe ^b  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG PURITY; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030561496     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00441-7     Document Type: Article

References (31)

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5. (d) Kagan, H. B. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Gordon, F., Stone, A., Eds.; Pergamon Press: New York, 1982; Vol 8, p 464.
6. 2. For leading references on the synthesis of o.p. phosphine oxides see: (a) Korpium, O; Mislow, K. J. Am. Chem. Soc. 1967, 89, 4784
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16. For recent review see: (k) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375.
17. 3. Alcudia, A.; Benabra, A.; Khiar, N.; Fernández, I.; Alcudia, F., Spanish Patent: Es 96/600573 (1996).
18. 4. For the first use of carbohydrates as chiral inducers in asymmetric synthesis at phosphorus see: Cooper, D. B.; Inch, T. D. Lewis, G. J. J. Chem. Soc., Perkin Trans, 1 1974, 1043.
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22. 6. Cholesterol instead of menthol has also been used as inducer of chirality with some but limited success see Nudelman, A.; Cram, D. J. J. Org. Chem. 1971, 36, 335.
23. 7. (a) A Δδ of 0.36 and 0.53ppm are observed in the case of H-2 and H-4 protons, respectively (3 δ (ppm): H-1 = 5.95, H-2 = 5.05, H-4 = 4.40; 4H-1 = 5.82, H-2 = 4.65, H-4 = 4.88), making the diastereomeric excess determination very easy,
24. (b) Similarly a Δδ of 0.32 and 0.57ppm are also observed for H-2 and H-4 in phosphinate esters 5 and 6.
25. 8. It is generally assumed that the base to be used in the synthesis of phosphinate esters from a secondary alcohol is pyridine.
26. 9. The reaction of Grignard reagents with mentylphosphinates was found to be very sensitive to the variation of the groups at phosphorus, oxygen, and magnesium, see ref 3b.
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