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Volumn , Issue , 2006, Pages 383-410

Chiral Bifunctional Acid/Base Catalysts

Author keywords

Chiral bifunctional acid base catalysts; Chiral Br nsted base catalysis; Chiral Lewis base catalysis

Indexed keywords


EID: 84889361944     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/0470098007.ch13     Document Type: Chapter
Times cited : (7)

References (165)
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    • For reviews on direct catalytic enantioselective aldol reactions, see Mahrwald, R. (Ed.), Wiley-VCH, Weinheim
    • For reviews on direct catalytic enantioselective aldol reactions, see: Shibasaki, M.; Matsunaga, S.; Kumagai, N. In Modern Aldol Reactions, Mahrwald, R. (Ed.), Wiley-VCH, Weinheim, 2004; Vol. 2, pp. 197-227
    • (2004) In Modern Aldol Reactions , vol.2 , pp. 197-227
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    • For the first example of direct catalytic asymmetric aldol reaction of ethyl ketones, see
    • For the first example of direct catalytic asymmetric aldol reaction of ethyl ketones, see Mahrwald, R.; Ziemer, B. Tetrahedron Lett. 2002, 43, 4459-4461.
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    • For reviews, see Jacobsen, E. N., Pfaltz, A., Yamamoto, H. (Eds.), Springer-Verlag, Heidelberg, Chap. 35
    • For reviews, see: Jacobsen, E. N.;Wu, M. H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H. (Eds.), Springer-Verlag, Heidelberg, 1999, Vol. III, Chap. 35
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  • 43
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    • A related reaction using an In-BINOL catalyst that can be applied to aromatic aldehydes has been reported:
    • A related reaction using an In-BINOL catalyst that can be applied to aromatic aldehydes has been reported: Takita, R.; Yakura, K.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 13760-13761.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 13760-13761
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    • this catalyst was extended to enantioselective allylsilylation of ketones:
    • this catalyst was extended to enantioselective allylsilylation of ketones: Wadamoto, M.; Yamamoto, H. J. Am. Chem. Soc. 2005, 127, 14556-14557.
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    • prior to the development of the catalytic enantioselective allyboration of ketones, we reported a catalytic enantioselective allylsilylation of ketones using CuF-tol-BINAP catalyst-in this allylsilylation, however, enantioselectivity was moderate:
    • prior to the development of the catalytic enantioselective allyboration of ketones, we reported a catalytic enantioselective allylsilylation of ketones using CuF-tol-BINAP catalyst-in this allylsilylation, however, enantioselectivity was moderate: Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536-6537.
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    • Other examples of catalytic enantioselective allylation reactions utilize chiral Lewis acid catalyst and allyltin reagents:
    • Other examples of catalytic enantioselective allylation reactions utilize chiral Lewis acid catalyst and allyltin reagents: Casolari, S.; D'Addario, D.; Tagliavini, E. Org. Lett. 1999, 1, 1061-1063
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    • For examples of catalytic enantioselective cyanation of ketones from other groups, see
    • For examples of catalytic enantioselective cyanation of ketones from other groups, see: Belokon', Y. N.; Green, B.; Ikonnikov, N. S.; North, M.; Tararov, V. I. Tetrahedron Lett. 1999, 38, 6669-6672
    • (1999) Tetrahedron Lett. , vol.38 , pp. 6669-6672
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    • For catalytic enantioselective synthesis of camptothecin intermediate, see
    • For catalytic enantioselective synthesis of camptothecin intermediate, see: Yabu, K.; Masumoto, S.; Kanai, M.; Curran, D. P.; Shibasaki, M. Tetrahedron Lett. 2002. 43, 2923-2926
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    • For fostriecin and its analog synthesis, see
    • Masumoto, S.; Suzuki, M.; Kanai, M.; Shibasaki, M. Tetrahedron 2004, 60, 10497-10504. For fostriecin and its analog synthesis, see:
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    • For catalytic enantioselective Strecker reaction of ketoimines from other groups, see: Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867-870
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    • for an extension of this catalyst to the first enantioselective meso-aziridine opening by cyanide, see
    • for an extension of this catalyst to the first enantioselective meso-aziridine opening by cyanide, see Mita, T.; Fujimori, I.; Wada, R.; Wen, J.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 11252-11253.
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    • For catalytic enantioselective conjugate addition of cyanide to a,b-unsaturated carbonyl compounds, see See also Ref. 25
    • For catalytic enantioselective conjugate addition of cyanide to a,b-unsaturated carbonyl compounds, see: Sammis, G. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 4442-4443. See also Ref. 25.
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    • For a review, see There are significant advances in catalytic enantioselective introduction of alkyl, vinyl, and phenyl groups to simple ketones using alkyltitanium reagents generated via in situ transmetalation from zinc to titanium. We did not mention these reactions in detail in this review, because the reaction mechanism still remains ambiguous if those reactions proceed through one-center catalysis or two-center catalysis. For selected examples, see
    • For a review, see: Ramón, D. J.; Yus, M. Angew. Chem. Int. Ed. 2004, 43, 284-287. There are significant advances in catalytic enantioselective introduction of alkyl, vinyl, and phenyl groups to simple ketones using alkyltitanium reagents generated via in situ transmetalation from zinc to titanium. We did not mention these reactions in detail in this review, because the reaction mechanism still remains ambiguous if those reactions proceed through one-center catalysis or two-center catalysis. For selected examples, see:
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    • Ramón, D.J.1    Yus, M.2
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    • For other examples of catalytic enantioselective alkynylation of a-ketoesters using a stoichiometric Zn metal, see
    • For other examples of catalytic enantioselective alkynylation of a-ketoesters using a stoichiometric Zn metal, see: Cozzi, P. G. Angew. Chem. Int. Ed. 2003, 42, 2895-2898
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    • Dimauro, E.F.1    Kozlowski, M.C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.