메뉴 건너뛰기




Volumn 28, Issue 14, 2009, Pages 4141-4149

Resolution of planar-chiral ferrocenylborane lewis acids: The impact of steric effects on the stereoselective binding of ephedrine derivatives

Author keywords

[No Author keywords available]

Indexed keywords

BIDENTATE LEWIS ACID; FERROCENE; FRACTIONAL CRYSTALLIZATION; ISOMERIC COMPLEX; LEWIS ACID; METHOXY; MULTINUCLEAR NMR; PSEUDOEPHEDRINE; SINGLE CRYSTAL X-RAY ANALYSIS; SINGLE CRYSTAL X-RAY DIFFRACTION ANALYSIS; STEREO-SELECTIVE; STEREOSELECTIVE COMPLEXATION; STERIC EFFECT; STERIC INTERACTIONS; TIME-SCALE; TIN CENTER;

EID: 67651014857     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900303j     Document Type: Article
Times cited : (15)

References (73)
  • 3
    • 33845184358 scopus 로고
    • (c) Midland, M. M. Chem. Rev. 1989, 89, 1553-1561.
    • (1989) Chem. Rev , vol.89 , pp. 1553-1561
    • Midland, M.M.1
  • 15
    • 0004205240 scopus 로고    scopus 로고
    • Davidson, M, Hughes, A. K, Marder, T. B, Wade, K, Eds, Royal Society of Chemistry: London
    • Soderquist, J. A. In Contemporary Boron Chemistry; Davidson, M., Hughes, A. K., Marder, T. B., Wade, K., Eds.; Royal Society of Chemistry: London, 2000.
    • (2000) Contemporary Boron Chemistry
    • Soderquist, J.A.1
  • 28
  • 32
  • 33
  • 35
    • 2442567748 scopus 로고    scopus 로고
    • (b) Fu, G. C. J. Org. Chem. 2004, 69, 3245-3249.
    • (2004) J. Org. Chem , vol.69 , pp. 3245-3249
    • Fu, G.C.1
  • 43
    • 0008205773 scopus 로고    scopus 로고
    • Short, R. P.; Masamune, S. J. Am. Chem. Soc. 1989, 111, 1892-1894. More recently, Soderquist has reported the use of pseudoephedrine derivatives for the resolution of B-methoxy-10-trimethylsilyl-9- borabicyclo[3.3.2]decane and related compounds:
    • (b) Short, R. P.; Masamune, S. J. Am. Chem. Soc. 1989, 111, 1892-1894. More recently, Soderquist has reported the use of pseudoephedrine derivatives for the resolution of B-methoxy-10-trimethylsilyl-9- borabicyclo[3.3.2]decane and related compounds:
  • 51
    • 67651029194 scopus 로고    scopus 로고
    • Unlike other boron pseudoephedrine chelates, which commonly display two signals in the 11B NMR in solution (indicating the existence of both open and closed forms, Rp-(1S,2S)-3 and Sp-(1S,2S)-3 display only one signal for the coordinated species; see ref 8
    • p-(1S,2S)-3 display only one signal for the coordinated species; see ref 8.
  • 52
    • 0037617789 scopus 로고    scopus 로고
    • n=1-6 are the bond angles at the boron center. See: Höpfl, H. J. Organomet. Chem. 1999, 581, 129-149.
    • n=1-6 are the bond angles at the boron center. See: Höpfl, H. J. Organomet. Chem. 1999, 581, 129-149.
  • 54
    • 84869535734 scopus 로고    scopus 로고
    • p-(1S,2S)-4 were isolated in 84% and 75% yield, respectively.
    • p-(1S,2S)-4 were isolated in 84% and 75% yield, respectively.
  • 55
    • 67651019831 scopus 로고    scopus 로고
    • Two signals for the diastereotopic N-methyl groups are observed as a result of the central chirality of the boron center
    • Two signals for the diastereotopic N-methyl groups are observed as a result of the central chirality of the boron center.
  • 57
    • 84869546829 scopus 로고    scopus 로고
    • p-( 1S,2S)-4a crystallizes with two independent molecules in the unit cell with similar geometrical parameters and two dichloromethane molecules in the crystal lattice.
    • p-( 1S,2S)-4a crystallizes with two independent molecules in the unit cell with similar geometrical parameters and two dichloromethane molecules in the crystal lattice.
  • 58
    • 67651032322 scopus 로고    scopus 로고
    • This decrease in bond distance is also reflected in the 119Sn NMR chemical shift of 22.4 ppm for Sp-2-(1S,2S)-PE vs 30.3 ppm for Sp-1(1S,2S)-PE
    • p-1(1S,2S)-PE.
  • 60
    • 67651026061 scopus 로고    scopus 로고
    • The N-Me signals (belonging to the same isomers) are found to be exchanging even at low temperatures
    • The N-Me signals (belonging to the same isomers) are found to be exchanging even at low temperatures.
  • 61
    • 84869546825 scopus 로고    scopus 로고
    • p-(1S,2S)-4b in solution.
    • p-(1S,2S)-4b in solution.
  • 72
    • 0004283944 scopus 로고    scopus 로고
    • Version 2, Multi-Scan Absorption Correction Program; University of Göttingen: Germany
    • Sheldrick, G. M. SADABS, Version 2, Multi-Scan Absorption Correction Program; University of Göttingen: Germany, 2001.
    • (2001) SADABS
    • Sheldrick, G.M.1
  • 73
    • 67651035528 scopus 로고    scopus 로고
    • Sheldrick, G. SHELXTL, Version 6.14; Bruker AXS Inc, Madison, WI, 2004
    • Sheldrick, G. SHELXTL, Version 6.14; Bruker AXS Inc.: Madison, WI, 2004.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.