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Volumn 5, Issue 18, 2003, Pages 3217-3220

Synthesis of substituted p-stereogenic vinylphosphine oxides by olefin cross-metathesis

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; OXIDE; PHOSPHINE DERIVATIVE; RUTHENIUM;

EID: 0141744713     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035011m     Document Type: Article
Times cited : (62)

References (50)
  • 4
    • 0034746687 scopus 로고    scopus 로고
    • Pertinent review: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (c) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (d) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037.
    • (2001) Acc. Chem. Res. , vol.34 , pp. 18
    • Trnka, T.M.1    Grubbs, R.H.2
  • 5
    • 0034746687 scopus 로고    scopus 로고
    • Pertinent review: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (c) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (d) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3012
    • Fürstner, A.1
  • 6
    • 0032580376 scopus 로고    scopus 로고
    • Pertinent review: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (c) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (d) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037.
    • (1998) Tetrahedron , vol.54 , pp. 4413
    • Grubbs, R.H.1    Chang, S.2
  • 7
    • 0034746687 scopus 로고    scopus 로고
    • Pertinent review: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (c) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (d) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 2037
    • Schuster, M.1    Blechert, S.2
  • 9
    • 0035940104 scopus 로고    scopus 로고
    • (b) For an olefin CM approach to vinylphosphonate-linked nucleic acids, cf.: Lera, M.; Hayes, C. J. Org. Lett. 2001, 3, 2765.
    • (2001) J. Org. Lett. , vol.3 , pp. 2765
    • Lera, M.1    Hayes, C.2
  • 10
    • 0034658902 scopus 로고    scopus 로고
    • (c) For a RCM reaction of P-chiral vinyl- and allylphosphonamides and phosphonates, see: Stoianova, D. S.; Hanson, P. R. Org. Lett. 2000, 2, 1769.
    • (2000) Org. Lett. , vol.2 , pp. 1769
    • Stoianova, D.S.1    Hanson, P.R.2
  • 22
    • 0035801862 scopus 로고    scopus 로고
    • (a) For a CM reaction of phenyl vinyl sulfone catalyzed by 1a, see: Grela, K.; Bieniek, M. Tetrahedron Lett. 2001, 42, 6425.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 6425
    • Grela, K.1    Bieniek, M.2
  • 23
    • 0037498252 scopus 로고    scopus 로고
    • (b) For screening of the catalytic performance of Ru- and Mo-based catalysts in this transformation, see: Grela, K.; Michrowska, A.; Bieniek, M.; Kim, M.; Klajn, R. Tetrahedron 2003, 59, 4525-4531.
    • (2003) Tetrahedron , vol.59 , pp. 4525-4531
    • Grela, K.1    Michrowska, A.2    Bieniek, M.3    Kim, M.4    Klajn, R.5
  • 26
    • 0141581489 scopus 로고    scopus 로고
    • Accepted for publication
    • (b) For applications of 1c, see ref 9b and: Ostrowski, S.; Mikus, A. Mol. Divers. Accepted for publication.
    • Mol. Divers
    • Ostrowski, S.1    Mikus, A.2
  • 28
    • 0141469819 scopus 로고    scopus 로고
    • note
    • Frequently, the terms "P-chiral" and "P-chirogenic" have been used to differentiate chiral phosphorus-containing compounds that bear a stereogenic phosphorus atom from those that do not. These terms are, however, incorret, and their use should be discouraged. We thank Prof. Scott E. Denmark for bringing this issue to our attention.
  • 42
    • 0141693067 scopus 로고    scopus 로고
    • note
    • 23OPNa): calcd 321.1379, found 321.1391.
  • 44
    • 0043098398 scopus 로고    scopus 로고
    • 1NMR using chiral shift reagents, which in these cases gave only moderate line separations (ca. 4-5 Hz, refs 22 and 23), the enantiomeric purity of the starting 3b was deliberately lowered to 73% by admixing of rac-3b.
    • (1996) Phosphorus, Sulfur, Silicon , vol.109 , pp. 573
    • Pietrusiewicz, K.M.1
  • 45
    • 0141469818 scopus 로고    scopus 로고
    • note
    • In homodimerization reaction of 3b, we have also isolated a theoretical yield (≈5%) of the phosphine oxide 6, a product of CM between 3b and catalyst 1c.
  • 50
    • 0141693066 scopus 로고    scopus 로고
    • note
    • 3, 500 MHz): δ (rel weight) = 6.29 (0.15), 6.27 (1.00); 6.26 (0.16), 6.24 (1.00); 6.20 (0.17), 6.19 (1.00); 1.10 (0.14), 1.08 (1.00); 1.07 (0.16), 1.05 (1.00). Calculated optical purity: 72 ± 4% ee.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.