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Volumn , Issue 4, 2007, Pages 599-602

Chiral P-chlorophospholane: A versatile building block for the synthesis of ligands

Author keywords

Ligands; Phosphorus; Phosphorylation; Stereoselective synthesis

Indexed keywords

1 CHLORO 2,5 DIMETHYLPHOSPHOLANE; OXAZOLINEPHOSPHOLANE DERIVATIVE; PHOSPHINE DERIVATIVE; PHOSPHORUS; PICOLINE DERIVATIVE; T TRIMETHYLSILYLPHOSPHOLANE; UNCLASSIFIED DRUG;

EID: 33947318080     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-967974     Document Type: Article
Times cited : (17)

References (26)
  • 1
    • 0000701744 scopus 로고    scopus 로고
    • For general reviews, see: a, Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer-Verlag: Berlin
    • For general reviews, see: (a) Brown, J. M. In Comprehensive Asymmetric Catalysis, Vol. I; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999, 121-182.
    • (1999) Comprehensive Asymmetric Catalysis , vol.1 , pp. 121-182
    • Brown, J.M.1
  • 4
    • 85196432391 scopus 로고    scopus 로고
    • For reviews on chiral phospholanes and other cyclic phosphines and their application in asymmetric catalysis, see: (a) Holz, J, Gensow, M.-N, Zayas, O, Börner, A. Curr. Org. Chem. 2007, 11, 61
    • For reviews on chiral phospholanes and other cyclic phosphines and their application in asymmetric catalysis, see: (a) Holz, J.; Gensow, M.-N.; Zayas, O.; Börner, A. Curr. Org. Chem. 2007, 11, 61.
  • 6
    • 0033918708 scopus 로고    scopus 로고
    • and references cited therein
    • Burk, M. J. Acc. Chem. Res. 2000, 33, 363; and references cited therein.
    • (2000) Acc. Chem. Res , vol.33 , pp. 363
    • Burk, M.J.1
  • 16
    • 33947328891 scopus 로고    scopus 로고
    • Other approaches are based on the cleavage of the P-phenyl bond by lithium or by deprotonation of the P-H bond in relevant phospholanes. The latter methods are frequently accompanied by the epimerization of the adjacent chiral C-atoms or the formation of side products and therefore are not suitable for the construction of optically pure ligands.10c,f
    • 10c,f
  • 17
    • 0001923067 scopus 로고
    • For other monophospholane derivatives as possible building blocks for coupling reactions, see: a
    • For other monophospholane derivatives as possible building blocks for coupling reactions, see: (a) Brunner, H.; Sievi, R. J. Organomet. Chem. 1987, 328, 71.
    • (1987) J. Organomet. Chem , vol.328 , pp. 71
    • Brunner, H.1    Sievi, R.2
  • 26
    • 33947317289 scopus 로고    scopus 로고
    • Solvents were dried and freshly distilled under argon before use. All reactions were performed under an argon atmosphere by using standard Schlenk techniques. 1H, 13C and 31P NMR spectra were recorded on a Bruker ARX 400 spectrometer at the following frequencies: 400.13 MHz (1H, 100.63 MHz (13C, 161.98 MHz (31P, 235 MHz (19F) with CDCl3 as solvent, R,R)-1- Chloro-2,5-dimethylphospholane (2) A solution of 1-trimethylsilyl-2,5- dimethyl-phospholane (1, 10.0 g, 53.1 mmol) in CH2Cl 2 (60 mL) was added via cannula to a solution of hexachloroethane (12.6 g, 53.1 mmol) in CH2Cl2 (80 mL) under stirring at ambient temperature. Then the mixture was stirred under reflux for 30 min. After cooling, the solvent and tetrachlorethene was removed in vacuo (500 mbar) and the residue was distilled to give chlorophospholane 2 7.40 g, 93, a
    • 2O (3 mL) was added.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.