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Volumn 68, Issue 11, 2003, Pages 4293-4301

Highly enantiomerically enriched chlorophosphine boranes: Synthesis and applications as P-chirogenic electrophilic blocks

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; CHROMATOGRAPHIC ANALYSIS; SILICA GEL; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 0038823978     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026355d     Document Type: Article
Times cited : (100)

References (64)
  • 15
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    • For selected examples of synthesis of phosphorus ligands using chlorophosphine as electrophilic blocks, see: (a) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 1769-1772
    • Sprinz, J.1    Helmchen, G.2
  • 17
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    • See also refs 4 and 5
    • (c) See also refs 4 and 5.
  • 19
    • 0034079675 scopus 로고    scopus 로고
    • For a pertinent review on monophosphines or derivative ligands, see: (a) Lagasse, F.; Kagan, H. B. Chem. Pharm. Bull. 2000, 48 (3), 315-324.
    • (2000) Chem. Pharm. Bull. , vol.48 , Issue.3 , pp. 315-324
    • Lagasse, F.1    Kagan, H.B.2
  • 25
    • 0032562612 scopus 로고    scopus 로고
    • For kinetic resolution studies of chlorophosphine 1, see: (a) Kolodiazhnyi, O. I. Tetrahedron 1998, 9, 1279-1332.
    • (1998) Tetrahedron , vol.9 , pp. 1279-1332
    • Kolodiazhnyi, O.I.1
  • 32
    • 0037652739 scopus 로고    scopus 로고
    • note
    • (b) For a recent review of borane decomplexation with amines, olefins, ethanol, or acids, see ref 16c.
  • 48
    • 0038666918 scopus 로고    scopus 로고
    • note
    • The high enantiomeric excesses obtained in most cases prove the stereospecificity of the organolithium reaction with the chlorophosphine boranes 4.
  • 49
    • 12044254595 scopus 로고    scopus 로고
    • For pertinent reviews on the stereochemistry of single nucleophilic displacement at P-chirogenic phosphinous derivatives, see: (a) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411. (b) Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 1998, 9, 1279-1332. In the case of phosphinous borane derivatives see: (a) ref 14c. (b) Brunel, J. M.; Faure, B.; Maffei, M. Coord. Chem. Rev. 1998, 178-180, 665-698.
    • (1994) Chem. Rev. , vol.94 , pp. 1375-1411
    • Pietrusiewicz, K.M.1    Zablocka, M.2
  • 50
    • 0032562612 scopus 로고    scopus 로고
    • For pertinent reviews on the stereochemistry of single nucleophilic displacement at P-chirogenic phosphinous derivatives, see: (a) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411. (b) Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 1998, 9, 1279-1332. In the case of phosphinous borane derivatives see: (a) ref 14c. (b) Brunel, J. M.; Faure, B.; Maffei, M. Coord. Chem. Rev. 1998, 178-180, 665-698.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 1279-1332
    • Kolodiazhnyi, O.I.1
  • 51
    • 12044254595 scopus 로고    scopus 로고
    • ref 14c
    • For pertinent reviews on the stereochemistry of single nucleophilic displacement at P-chirogenic phosphinous derivatives, see: (a) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411. (b) Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 1998, 9, 1279-1332. In the case of phosphinous borane derivatives see: (a) ref 14c. (b) Brunel, J. M.; Faure, B.; Maffei, M. Coord. Chem. Rev. 1998, 178-180, 665-698.
  • 52
    • 0032275043 scopus 로고    scopus 로고
    • For pertinent reviews on the stereochemistry of single nucleophilic displacement at P-chirogenic phosphinous derivatives, see: (a) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411. (b) Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 1998, 9, 1279-1332. In the case of phosphinous borane derivatives see: (a) ref 14c. (b) Brunel, J. M.; Faure, B.; Maffei, M. Coord. Chem. Rev. 1998, 178-180, 665-698.
    • (1998) Coord. Chem. Rev. , vol.178-180 , pp. 665-698
    • Brunel, J.M.1    Faure, B.2    Maffei, M.3
  • 53
    • 0007842575 scopus 로고    scopus 로고
    • 11 For an example of calculations involving pentacoordinate phosphorus borane adducts, see: Solling, T. I.; Wild, S. B.; Radom, L. J. Organomet. Chem. 1999, 580, 320-327.
    • (1999) Organomet. Chem. , vol.580 , pp. 320-327
    • Solling, T.I.1    Wild, S.B.2    Radom, L.J.3
  • 56
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    • note
    • 20


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