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Volumn 126, Issue 39, 2004, Pages 12236-12237

Catalytic asymmetric hydroxymethylation of silicon enolates using an aqueous solution of formaldehyde with a chiral scandium complex

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; ENOLATE; ETHANE; ETHYLENE GLYCOL DIMETHYL ETHER; FORMALDEHYDE; LEWIS ACID; MONOMER; PARAFORMALDEHYDE; SCANDIUM; SILICON DERIVATIVE; SILICON ENOLATE; SOLVENT; TRIOXANE; UNCLASSIFIED DRUG;

EID: 4644286223     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047896i     Document Type: Article
Times cited : (162)

References (27)
  • 4
    • 0005696762 scopus 로고    scopus 로고
    • Bellus, D., Ley, S. V., Noyori, R., Regitz, M., Schaumann, E., Shinkai, I., Thomas, E., J., Trost, B. M., Eds.; Georg Thieme Verlag: Stuttgart
    • For a review on silicon enolates, see: Kobayashi, S.; Manabe, K.; Ishitani, H.; Matsuo, J. In Science of Synthesis, Houben-Weyl Methods of Molecular Transformation; Bellus, D., Ley, S. V., Noyori, R., Regitz, M., Schaumann, E., Shinkai, I., Thomas, E., J., Trost, B. M., Eds.; Georg Thieme Verlag: Stuttgart, 2002; Vol. 4, p 317.
    • (2002) Science of Synthesis, Houben-Weyl Methods of Molecular Transformation , vol.4 , pp. 317
    • Kobayashi, S.1    Manabe, K.2    Ishitani, H.3    Matsuo, J.4
  • 6
    • 0001702357 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pflatz, A., Yamamoto, H., Eds.; Springer; Heidelberg
    • (b) Carreira, E. M. Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pflatz, A., Yamamoto, H., Eds.; Springer; Heidelberg, 1999; Vol. 3, p 998.
    • (1999) Comprehensive Asymmetric Catalysis , vol.3 , pp. 998
    • Carreira, E.M.1
  • 10
    • 45549119177 scopus 로고
    • For hydroxymethylation of a silicon enolate in aqueous media without any catalysts, see: (b) Lubineau, A.; Meyer, E. Tetrahedron 1988, 44, 6065.
    • (1988) Tetrahedron , vol.44 , pp. 6065
    • Lubineau, A.1    Meyer, E.2
  • 17
    • 0013220495 scopus 로고
    • 2,6-Di-tert-butylpyridine was used as an additive for Lewis acid-catalyzed aldol reactions. For example: (a) Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988, 44, 4275.
    • (1988) Tetrahedron , vol.44 , pp. 4275
    • Murata, S.1    Suzuki, M.2    Noyori, R.3
  • 19
    • 33751157649 scopus 로고
    • Also see: ref 10b
    • It is also noteworthy that water is essential in this reaction. To see the effects of water in this catalytic system, we performed an asymmetric aldol reaction of benzaldehyde where anhydrous conditions were easy to access. While the reaction of benzaldehyde with 2 in H20/DME (1:9) at -20 °C for 21 h proceeded smoothly with good yield (76%) and modest selectivity (syn/anti = 78/22, 59% ee (syn)) using 10 mol % of the chiral Sc catalyst, the reaction in DME without water did not proceed at all (-20 °C, 24 h). This result indicates that water plays an important role for the catalytic activity in this system. For effects of water in rare earth metal triflate-catalyzed aldol reactions, see: Kobayashi, S.; Hachiya, I. J. Org. Chem. 1994, 59, 3590. Also see: ref 10b.
    • (1994) J. Org. Chem. , vol.59 , pp. 3590
    • Kobayashi, S.1    Hachiya, I.2
  • 20
    • 4644373280 scopus 로고    scopus 로고
    • note
    • 3: 22 h, 75% yield, 83% ee).
  • 25
    • 0001567028 scopus 로고    scopus 로고
    • For reviews on catalytic asymmetric carbon-carbon bond-forming reactions in aqueous media, see: (a) Sinou, D. Adv. Synth. Catal. 2002, 344, 221.
    • (2002) Adv. Synth. Catal. , vol.344 , pp. 221
    • Sinou, D.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.