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Volumn 59, Issue 44, 2003, Pages 8821-8825

A two step synthesis of 2-oxo-2-vinyl 1,3,2-dioxaphospholanes and -dioxaphosphorinanes

Author keywords

2 oxo 2 vinyl 1,3,2 dioxaphospholanes; 2 oxo 2 vinyl 1,3,2 dioxaphosphorinanes; DFT calculations; Palladium; Transesterification; Vinyl bromide

Indexed keywords

2 OXO 2 VINYL 1,3,2 DIOXAPHOSPHORINANE; 4,4,5,5 TETRAMETHYL 2 OXO 2 VINYL 1,3,2 DIOXAPHOSPHALANE; 5,5 DIMETHYL 2 OXO 2 VINYL 1,3,2 DIOXAPHOSPHORINANE; BIS(BENZYLOXYMETHYL) 2 OXO 2 VINYL 1,3,2 DIOXOPHOSPHOLANE; BIS(METHOXYMETHYL) 2 OXO 2 VINYL 1,3,2 DIOXAPHOSPHOLANE; DIETHYLPHOSPHITE; PALLADIUM; PHOSPHITE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYLBROMIDE;

EID: 0141961791     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.08.067     Document Type: Article
Times cited : (38)

References (56)
  • 3
    • 0031997839 scopus 로고    scopus 로고
    • and references cited therein
    • (b) Jin S., Gonsalves K.E. Macromolecules. 31:1998;1010. and references cited therein.
    • (1998) Macromolecules , vol.31 , pp. 1010
    • Jin, S.1    Gonsalves, K.E.2
  • 21
    • 85031056792 scopus 로고
    • (b) Yuldashev A., Abidov S.T. Dokl. Akad. Nauk SSSR. 23:1966;36. Chem. Abstr. 1967, 66, 86180f
    • (1967) Chem. Abstr. , vol.66
  • 25
  • 28
    • 85031054898 scopus 로고    scopus 로고
    • (c) For the vinylation of chiral diazaphospholidines see Ref. 4e
    • (c) For the vinylation of chiral diazaphospholidines see Ref. 4e.
  • 34
    • 0003793533 scopus 로고    scopus 로고
    • For the synthesis of 1,4-di-O-protected L-threitols and their derivatives see. J. Gawronski, & K. Gawronska. New York: Wiley-Interscience
    • For the synthesis of 1,4-di-O-protected L-threitols and their derivatives see Gawronski J., Gawronska K. Tartaric and Malic Acids in Synthesis. 1999;310 Wiley-Interscience, New York.
    • (1999) Tartaric and Malic Acids in Synthesis , pp. 310
  • 35
    • 0022374625 scopus 로고
    • Chiral cyclic phosphites have been used in asymmetric additions to heterocyclic imines: (a) Hoppe I., Schöllkopf U., Nieger M., Egert E. Angew. Chem., Int. Ed. Engl. 24:1985;1067 (b) Schlemminger I., Willecke A., Maison W., Koch R., Lützen A., Martens J. J. Chem. Soc., Perkin Trans. 2001;2804. and references cited therein. Use in asymmetric phospha-Michael additions: (c) Enders D., Tedeschi L., Bats J.W. Angew. Chem., Int. Ed. Engl. 39:2000;4605 (d) Enders D., Tedeschi L. Org. Lett. 3:2001;3515.
    • (1985) Angew. Chem., Int. Ed. Engl. , vol.24 , pp. 1067
    • Hoppe, I.1    Schöllkopf, U.2    Nieger, M.3    Egert, E.4
  • 36
    • 0034740251 scopus 로고    scopus 로고
    • Chiral cyclic phosphites have been used in asymmetric additions to heterocyclic imines: (a) Hoppe I., Schöllkopf U., Nieger M., Egert E. Angew. Chem., Int. Ed. Engl. 24:1985;1067 (b) Schlemminger I., Willecke A., Maison W., Koch R., Lützen A., Martens J. J. Chem. Soc., Perkin Trans. 2001;2804. and references cited therein. Use in asymmetric phospha-Michael additions: (c) Enders D., Tedeschi L., Bats J.W. Angew. Chem., Int. Ed. Engl. 39:2000;4605 (d) Enders D., Tedeschi L. Org. Lett. 3:2001;3515.
    • (2001) J. Chem. Soc., Perkin Trans. , pp. 2804
    • Schlemminger, I.1    Willecke, A.2    Maison, W.3    Koch, R.4    Lützen, A.5    Martens, J.6
  • 37
    • 0034671515 scopus 로고    scopus 로고
    • Chiral cyclic phosphites have been used in asymmetric additions to heterocyclic imines: (a) Hoppe I., Schöllkopf U., Nieger M., Egert E. Angew. Chem., Int. Ed. Engl. 24:1985;1067 (b) Schlemminger I., Willecke A., Maison W., Koch R., Lützen A., Martens J. J. Chem. Soc., Perkin Trans. 2001;2804. and references cited therein. Use in asymmetric phospha-Michael additions: (c) Enders D., Tedeschi L., Bats J.W. Angew. Chem., Int. Ed. Engl. 39:2000;4605 (d) Enders D., Tedeschi L. Org. Lett. 3:2001;3515.
    • (2000) Angew. Chem., Int. Ed. Engl. , vol.39 , pp. 4605
    • Enders, D.1    Tedeschi, L.2    Bats, J.W.3
  • 38
    • 0035516197 scopus 로고    scopus 로고
    • Chiral cyclic phosphites have been used in asymmetric additions to heterocyclic imines: (a) Hoppe I., Schöllkopf U., Nieger M., Egert E. Angew. Chem., Int. Ed. Engl. 24:1985;1067 (b) Schlemminger I., Willecke A., Maison W., Koch R., Lützen A., Martens J. J. Chem. Soc., Perkin Trans. 2001;2804. and references cited therein. Use in asymmetric phospha-Michael additions: (c) Enders D., Tedeschi L., Bats J.W. Angew. Chem., Int. Ed. Engl. 39:2000;4605 (d) Enders D., Tedeschi L. Org. Lett. 3:2001;3515.
    • (2001) Org. Lett. , vol.3 , pp. 3515
    • Enders, D.1    Tedeschi, L.2
  • 39
    • 0003670183 scopus 로고
    • 31P) values and useful information concerning bond angles at phosphorus in cyclic systems is not in general reliable available from chemical shift data: J.G. Verkade, & L.D. Quin. Florida: VCH. Chapter 9
    • 31P) values and useful information concerning bond angles at phosphorus in cyclic systems is not in general reliable available from chemical shift data: Gallagher M.J. Verkade J.G., Quin L.D. Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis. 1987;297 VCH, Florida. Chapter 9.
    • (1987) Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis , pp. 297
    • Gallagher, M.J.1
  • 50
    • 85031057484 scopus 로고    scopus 로고
    • Calculated extracyclic P-O bond lengths: C′ P-Oax 1.527 Å, D′ P-Oeq 1.512 Å, E′ P-O 1.519 Å
    • Calculated extracyclic P-O bond lengths: C′ P-Oax 1.527 Å, D′ P-Oeq 1.512 Å, E′ P-O 1.519 Å
  • 55
    • 0034616854 scopus 로고    scopus 로고
    • It is worth noting a reverse reactivity for the cyclic hydrogen phosphites in the palladium catalyzed hydrophosphorylation of alkenes but this reaction proceeds by a different mechanism in which the rate-limiting step is the reductive elimination Han L.-B., Mirzaei F., Zhao C.-Q., Tanaka M. J. Am. Chem. Soc. 122:2000;5407.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 5407
    • Han, L.-B.1    Mirzaei, F.2    Zhao, C.-Q.3    Tanaka, M.4
  • 56
    • 0141940336 scopus 로고
    • The term stereoelectronic effect has become synonymous with an effect otherwise termed the kinetic anomeric effect or the antiperiplanar lone pair hypothesis Thatcher G.R.J., Kluger R. Bethell D. Advances in Physical Organic Chemistry. Vol. 25:1989;171 Academic, New York.
    • (1989) Advances in Physical Organic Chemistry , vol.25 , pp. 171
    • Thatcher, G.R.J.1    Kluger, R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.