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Volumn , Issue 36, 2008, Pages 4309-4311

Lewis base-catalyzed conjugate reduction and reductive aldol reaction of α,β-unsaturated ketones using trichlorosilane

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; HEMPA; KETONE DERIVATIVE; LEWIS BASE; SILANE DERIVATIVE; TRICHLOROSILANE; UNCLASSIFIED DRUG;

EID: 52649107590     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b807529h     Document Type: Article
Times cited : (122)

References (25)
  • 11
    • 33750084396 scopus 로고    scopus 로고
    • For related reactions based on non-metal-catalyzed hydrostannation, see:
    • N. J. A. Matrin B. List J. Am. Chem. Soc. 2006 128 13368
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 13368
    • Matrin, N.J.A.1    List, B.2
  • 13
    • 0001639833 scopus 로고    scopus 로고
    • A catalytic asymmetric reductive Michael cyclization has been reported, see:
    • D. S. Hays M. Scholl G. C. Fu J. Org. Chem. 1996 61 6751
    • (1996) J. Org. Chem. , vol.61 , pp. 6751
    • Hays, D.S.1    Scholl, M.2    Fu, G.C.3
  • 14
    • 27544489337 scopus 로고    scopus 로고
    • Trichlorosilane has been utilized for (asymmetric) 1,2-reduction of aldehydes, ketones, aldimines and ketimines in combination with (chiral) Lewis base-catalysts. For leading references, see:
    • J. W. Yang M. T. H. Fonseca B. List J. Am. Chem. Soc. 2005 127 15036
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 15036
    • Yang, J.W.1    Fonseca, M.T.H.2    List, B.3
  • 20
    • 34447331272 scopus 로고    scopus 로고
    • Cobalt(ii) chloride-catalyzed 1,4-reduction of enones or acryl esters with trichlorosilane has been reported, see:
    • L. Zhou Z. Wang S. Wei J. Sun Chem. Commun. 2007 2977
    • (2007) Chem. Commun. , pp. 2977
    • Zhou, L.1    Wang, Z.2    Wei, S.3    Sun, J.4
  • 21
    • 85047677817 scopus 로고    scopus 로고
    • For a palladium-catalyzed reductive aldol reaction with trichlorosilane, see ref. 1c A patent that describes a formamide-catalyzed conjugate reduction of enones with the silane has been reported, see: Y. Matsumira and F. Iwasaki, Jpn. Pat., JP 2003171334 A. However, this patent does not describe the effect of Lewis bases other than formamides. Formamides are generally effective in the reduction of aldehydes with trichlorosilane, see ref. 4 For a pioneering study on aldol reaction of trichlorosilyl enolates, see:
    • M. Chauhan P. Boudjouk Can. J. Chem. 2000 78 1396
    • (2000) Can. J. Chem. , vol.78 , pp. 1396
    • Chauhan, M.1    Boudjouk, P.2
  • 23
    • 52649177906 scopus 로고    scopus 로고
    • 1H NMR study of the reaction of benzalacetone with trichlorosilane in deuterated dichloromethane confirmed the formation of the corresponding (Z)-trichlorosilyl enolate (assigned by a NOESY experiment), which supports a six-membered cyclic transition state with the s-cis conformation of enones (Figure). A similar mechanism has been suggested for borane reduction, see:
    • 1H NMR analysis of the crude reaction mixture using dibenzyl ether as an internal standard
  • 24
    • 0001595774 scopus 로고
    • Low diastereoselectivities (dr = 50: 50 to 78: 22) were observed in each case probably due to contributions of both catalyzed and non-catalyzed aldol processes, see ref. 7 We have employed BINAPO as a chiral Lewis base catalyst for enantioselective allylation, aldol reaction and epoxide ring-opening reaction, see:
    • G. P. Boldrini M. Bortolotti F. Mancini E. Tagliavini C. Trombini A. Umani-Ronchi J. Org. Chem. 1991 56 5820
    • (1991) J. Org. Chem. , vol.56 , pp. 5820
    • Boldrini, G.P.1    Bortolotti, M.2    Mancini, F.3    Tagliavini, E.4    Trombini, C.5    Umani-Ronchi, A.6
  • 25
    • 33847632961 scopus 로고    scopus 로고
    • The minor anti-isomer is racemic, which is consistent with the fact that the non-catalyzed aldol process favors the anti-product in a similar system, see ref. 7
    • S. Kotani S. Hashimoto M. Nakajima Tetrahedron 2007 63 3122
    • (2007) Tetrahedron , vol.63 , pp. 3122
    • Kotani, S.1    Hashimoto, S.2    Nakajima, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.