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Volumn , Issue 17, 2007, Pages 2808-2814

Stereochemistry and construction of tetrasubstituted chiral carbon centers in intramolecular Pd-catalyzed 1,3-chirality transfer reactions

Author keywords

1,3 chirality transfer; Pd II catalyzed cyclization; Spiro compounds; Tetrahydropyran; Tetrasubstituted chiral carbon

Indexed keywords


EID: 34250890129     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200601103     Document Type: Article
Times cited : (38)

References (31)
  • 8
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    • general review on the synthesis of tetrahydropyrans; a M. C. Elliott, E. Williams, J. Chem. Soc., Perkin Trans. 1 2001, 2303-2340;
    • general review on the synthesis of tetrahydropyrans; a) M. C. Elliott, E. Williams, J. Chem. Soc., Perkin Trans. 1 2001, 2303-2340;
  • 15
    • 0042535874 scopus 로고    scopus 로고
    • M. Schlosser, John Wiley and Sons, New York, 2nd Ed, p
    • a) L. S. Hegedus, in: M. Schlosser, Organometallics in Synthesis, John Wiley and Sons, New York, 2002, 2nd Ed., p. 1123;
    • (2002) Organometallics in Synthesis , pp. 1123
    • Hegedus, L.S.1
  • 19
    • 33749017670 scopus 로고    scopus 로고
    • In comparison with other methods for the synthesis of tetrahydropyrans it is noteworthy that 2,6-cis- and -trans-substituted tetrahydropyrans are formed with similar efficiency. The synthesis of trans-tetrahydropyrans in particular is often not trivial (for a recent successful example, refer to S. Roth, C. B. W. Stark, Angew. Chem. Int. Ed. 2006, 45, 6218-6221.)
    • In comparison with other methods for the synthesis of tetrahydropyrans it is noteworthy that 2,6-cis- and -trans-substituted tetrahydropyrans are formed with similar efficiency. The synthesis of trans-tetrahydropyrans in particular is often not trivial (for a recent successful example, refer to S. Roth, C. B. W. Stark, Angew. Chem. Int. Ed. 2006, 45, 6218-6221.)
  • 24
    • 34250845696 scopus 로고    scopus 로고
    • Physical data for compound 7′. Colorless oil, a] D22, 19.9 (c, 1.00, CHCl3, Rf, 0.34 (hexane/Et2O, 75:25, 1H NMR (300 MHz, CDCl3, 25 °C, δ, 0.05 (s, 6 H, CH 3Si, 0.89 (s, 9 H, CH3CSi, 1.03-1.31 (m, 5H, 1.12 (d, J, 6.1 Hz, 3 H, CH3, 143-1.86 (m, 11 H, 2.19-2.24 (m, 2 H, 3.80 (m, 1 H, CHOH, 4.13 (m, 1H, CHOH) ppm. 13C NMR (75 MHz, CDCl3, 25 °C, δ, 4.8 (CH3, 4.4 (CH3, 18.1 (C, 18.8, 23.8, 25.0, 25.9, 25.9, 26.4, 28.1, 28.6, 38.8, 44.4, 67.4, 68.1, 80.3, 86.1 ppm. IR: ṽ, 3376, 2927, 2855, 1450, 1374, 1255, 1187, 1137, 1092, 1023, 893, 836, 774 cm -1. MS (CI, mlz, 339 (0.9, M, H, 321 (14.8, 281 (6.8, 189 (100, HRMS CI, C20H39O 2Si calcd. 339.2719
    • 2Si calcd. 339.2719; found 339.2712.
  • 25
    • 34250883120 scopus 로고    scopus 로고
    • In compounds 7, 8, 9, 13, 14, and 4 there were no differences except for their degrees of optical rotation in the spectroscopic data for their (R) and (S) diastereoisomers.
    • In compounds 7, 8, 9, 13, 14, and 4 there were no differences except for their degrees of optical rotation in the spectroscopic data for their (R) and (S) diastereoisomers.
  • 26
    • 34250843007 scopus 로고    scopus 로고
    • Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, Germany
    • A. de Meijere, F. Diederich, Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, Germany, 2004, volumes 1 and 2.
    • (2004) volumes 1 and 2
    • de Meijere, A.1    Diederich, F.2
  • 29
    • 34250798906 scopus 로고    scopus 로고
    • Their des were less than 50%.
    • Their des were less than 50%.
  • 31
    • 34250831315 scopus 로고    scopus 로고
    • -1, detection: 254 nm, retention time: 12.7 min [13 (R) isomer], 19.1 min [13′ (S) isomer].
    • -1, detection: 254 nm, retention time: 12.7 min [13 (R) isomer], 19.1 min [13′ (S) isomer].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.