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Volumn 18, Issue 14, 2012, Pages 4401-4410

Cross-coupling reactions of organosilicon compounds in the stereocontrolled synthesis of retinoids

Author keywords

C C coupling; organic synthesis; retinoids; silicon; stereochemistry

Indexed keywords

C-C COUPLING; COMPREHENSIVE STUDIES; CONVERGENT APPROACH; CROSS COUPLING REACTIONS; ELECTROPHILES; ETHOXYSILANES; GOOD YIELD; HIYAMA CROSS-COUPLING REACTION; MILD REACTION CONDITIONS; ORGANIC SYNTHESIS; ORGANOSILICON COMPOUNDS; PALLADIUM CATALYST; RETINOIDS; SILANOLS; SILICON-BASED; SILYL HYDRIDES; STEREOCONTROLLED SYNTHESIS; STERIC CONGESTION;

EID: 84859342689     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201103360     Document Type: Article
Times cited : (32)

References (142)
  • 31
    • 20544450502 scopus 로고    scopus 로고
    • 2 nd ed. (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim
    • Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed., (Eds.: A. de Meijere, F. Diederich,), Wiley-VCH, Weinheim, 2004.
    • (2004) Metal-Catalyzed Cross-Coupling Reactions
  • 58
    • 72949108920 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 9240-9261; for the use of air and moisture-stable N-methyliminodiacetic acid (MIDA) boronates in retinal synthesis, see
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 9240-9261
  • 61
    • 0000390817 scopus 로고    scopus 로고
    • (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, Chapter 10
    • T. Hiyama, in Metal-Catalyzed Cross-Coupling Reactions (Eds.:, F. Diederich, P. J. Stang,), Wiley-VCH, Weinheim, 1998, Chapter 10, p. 421
    • (1998) Metal-Catalyzed Cross-Coupling Reactions , pp. 421
    • Hiyama, T.1
  • 72
    • 77951169903 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 2978-2986.
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 2978-2986
  • 79
    • 21244463025 scopus 로고    scopus 로고
    • Denmark has prepared a tetraenoate intermediate (in the synthesis of RK-397) by sequential palladium-catalysed cross-coupling of a 1,4-bissilyl-1,3-butadiene. However, a mixture of olefin isomers was achieved:, S. E. Denmark, S. Fujimori, J. Am. Chem. Soc. 2005, 127, 8971-8973.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 8971-8973
    • Denmark, S.E.1    Fujimori, S.2
  • 80
    • 33845277870 scopus 로고
    • Trialkyl- and fluoroalkenylsilanes were not tested because of their low reactivity and their sensitivity to moisture, acids and bases, respectively:, Y. Hatanaka, T. Hiyama, J. Org. Chem. 1988, 53, 918-920
    • (1988) J. Org. Chem. , vol.53 , pp. 918-920
    • Hatanaka, Y.1    Hiyama, T.2
  • 81
    • 42749092334 scopus 로고    scopus 로고
    • Tris(trimethylsilyl)silanes were also not considered because they are known to suffer low stereoselectivity in the coupling of the Z isomers:, Z. Wang, J. Pitteloud, L. Montes, M. Rapp, D. Derane, S. F. Wnuk, Tetrahedron 2008, 64, 5322-5327.
    • (2008) Tetrahedron , vol.64 , pp. 5322-5327
    • Wang, Z.1    Pitteloud, J.2    Montes, L.3    Rapp, M.4    Derane, D.5    Wnuk, S.F.6
  • 108
    • 27744469211 scopus 로고    scopus 로고
    • Pd (dihydrosilanes)
    • Y. Yamanoi, J. Org. Chem. 2005, 70, 9607-9609; Pd (dihydrosilanes)
    • (2005) J. Org. Chem. , vol.70 , pp. 9607-9609
    • Yamanoi, Y.1
  • 140
    • 78650642360 scopus 로고    scopus 로고
    • Sequential processes involving silicon-based cross-couplings and their application to the total syntheses of natural products have been recently reviewed:, S. E. Denmark, J. H.-C. Liu, Isr. J. Chem. 2010, 50, 577-587.
    • (2010) Isr. J. Chem. , vol.50 , pp. 577-587
    • Denmark, S.E.1    Liu, J.H.-C.2
  • 142
    • 36048952708 scopus 로고    scopus 로고
    • Wagner has reported an efficient bimetallic polyionic-gel [Rh-Pd] catalyst that effects the same sequential protocol:, C. Thiot, M. Schmutz, A. Wagner, C. Mioskowski, Chem. Eur. J. 2007, 13, 8971-8978.
    • (2007) Chem. Eur. J. , vol.13 , pp. 8971-8978
    • Thiot, C.1    Schmutz, M.2    Wagner, A.3    Mioskowski, C.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.