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Volumn 71, Issue 17, 2006, Pages 6474-6484

3,3′-diphosphoryl-1,1′-bi-2-naphthol-Zn(II) complexes as conjugate acid-base catalysts for enantioselective dialkylzinc addition to aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYSIS; CATALYSTS; CHEMICAL BONDS; NUCLEAR MAGNETIC RESONANCE; ORGANIC ACIDS; REACTION KINETICS; X RAY ANALYSIS; ZINC COMPOUNDS;

EID: 33747396156     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060908t     Document Type: Article
Times cited : (110)

References (100)
  • 1
    • 0003445429 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin
    • (a) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Comprehensive Asymmetric Catalysis I-III; Springer: Berlin, 1999.
    • (1999) Comprehensive Asymmetric Catalysis I-III
  • 3
    • 0026418434 scopus 로고
    • (a) Trost, B. M. Science 1991, 254, 1471-1477.
    • (1991) Science , vol.254 , pp. 1471-1477
    • Trost, B.M.1
  • 8
    • 4244117250 scopus 로고
    • Reviews for catalytic enantioselective dialkylzinc additions to aldehydes and ketones: (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856.
    • (1992) Chem. Rev. , vol.92 , pp. 833-856
    • Soai, K.1    Niwa, S.2
  • 11
    • 0242635970 scopus 로고    scopus 로고
    • (d) Pu, L. Tetrahedron 2003, 59, 9873-9886.
    • (2003) Tetrahedron , vol.59 , pp. 9873-9886
    • Pu, L.1
  • 38
  • 44
  • 46
    • 0004231121 scopus 로고    scopus 로고
    • Wiley: New York, and the references therein
    • + have been studied. For an excellent textbook on organophosphorus chemistry see Quin, L. D. A Guide to Organophosphorus Chemistry; Wiley: New York, 2000, and the references therein.
    • (2000) A Guide to Organophosphorus Chemistry
    • Quin, L.D.1
  • 81
    • 33747414424 scopus 로고    scopus 로고
    • note
    • 2Zn to benzaldehyde gave low conversion (29% yield) and moderate enantioselectivity (71% ee) for 120 h.
  • 88
    • 33747404554 scopus 로고    scopus 로고
    • note
    • 2 = 10]. As discussed later in this paper, that central coordination should be critical for a transition-state assembly in diethylzinc addition (i.e., 37).
  • 91
    • 33747416728 scopus 로고    scopus 로고
    • note
    • 31P NMR.
  • 92
    • 33747387974 scopus 로고    scopus 로고
    • note
    • Certainly 34 and 35 are sterically very different. However, these results could reflect our assumption described, because a preliminary examination by using the model compound, a t-Bu group ortho to the OH in 34, also resulted in poor reactivities (20 mol%, room temperature, 24 h, 48% yield).
  • 93
    • 33747425209 scopus 로고    scopus 로고
    • note
    • For the nonflat model like Figure 11b, considerable interaction between vacant d-orbital of phosphorous and π-orbital of 2-naphthol is also possible. See refs 13 and 14.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.