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Volumn , Issue 5, 1999, Pages 1099-1105

Totally regio- and stereoselective P-O-to-P-C rearrangement in the synthesis of chiral P-(o-hydroxyaryl)diazaphospholidine P-oxides

Author keywords

Asymmetric synthesis; Chiral synthons; P (o Hydroxyaryl)diazaphospholidine P oxides; Rearrangements

Indexed keywords

PHOSPHONIC ACID DERIVATIVE;

EID: 0032766219     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199905)1999:5<1099::AID-EJOC1099>3.0.CO;2-R     Document Type: Article
Times cited : (22)

References (37)
  • 2
    • 0345032558 scopus 로고    scopus 로고
    • note
    • [5] have described the synthesis of such chiral compounds in low chemical yields, starting from (-)-ephedrine.
  • 13
    • 0344912805 scopus 로고
    • These compounds may be viewed as analogs of 1,3-diketone-type ligands of various transition metals. They may form complexes with metal ions and have been used in the preparation of ligands capable of extracting ammonium compounds from aqueous to organic phases: A. H. Alberts, K. Timmer, J. G. Noltes, A. L. Spek, J. Am. Chem. Soc. 1979, 101, 3375.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 3375
    • Alberts, A.H.1    Timmer, K.2    Noltes, J.G.3    Spek, A.L.4
  • 22
    • 0344601619 scopus 로고    scopus 로고
    • note
    • [11][12]
  • 27
    • 0000166427 scopus 로고
    • The classification of the diastereomers as syn and anti relates to the orientation of the methylene substituent of the pyrrolidine ring with respect to the extracyclic aryl group. If both are on the same side of the five-membered phosphorus-containing ring, we call it a syn diastereomer; otherwise, it is an anti diastereomer. [13a] P. Cros, G. Buono, G. Peiffer, D. Denis, A. Mortreux, F. Petit, New. J. Chem. 1987, 11, 573.
    • (1987) New. J. Chem. , vol.11 , pp. 573
    • Cros, P.1    Buono, G.2    Peiffer, G.3    Denis, D.4    Mortreux, A.5    Petit, F.6
  • 30
    • 0344169967 scopus 로고    scopus 로고
    • note
    • [15] (formula presented) Scheme 3. Mechanism for the stereoselective P-O-to-P-C rearrangement
  • 32
    • 0345032550 scopus 로고    scopus 로고
    • note
    • In the case of the 1a rearrangement, we did not observe the formation of the P-(m-hydroxyaryl)diazaphospholidine P-oxide adduct 2a′. The latter might have resulted from an ortho-directed metallation followed by an intermolecular nucleophilic substitution on the phosphoryl group.
  • 33
    • 0344601614 scopus 로고    scopus 로고
    • note
    • 1 from the systematic absences. A total of 1635 reflections were collected at T = 298 K. The standards were measured after every 120 reflections. Among the first 200 pairs of reflections, the signs of the corresponding calculated differences established that the molecule had been described with the correct absolute configuration (S).
  • 34
    • 0345463623 scopus 로고    scopus 로고
    • note
    • 1 from the systematic absences. A total of 1749 reflections were collected at T = 298 K. The standards were measured after every 120 reflections. Among the first 200 pairs of reflections, the signs of the corresponding calculated differences established that the molecule had been described with the correct absolute configuration (S).
  • 35
    • 0345463620 scopus 로고    scopus 로고
    • note
    • [4c]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.