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Volumn 71, Issue 4, 2006, Pages 1458-1463

Structurally simple pyridine N-oxides as efficient organocatalysts for the enantioselective allylation of aromatic aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; AMINO ACIDS; MOLECULAR STRUCTURE; OXIDES; SILANES;

EID: 33644508331     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052132m     Document Type: Article
Times cited : (80)

References (35)
  • 4
    • 0037251137 scopus 로고    scopus 로고
    • and references therein
    • For leading references to the use of Lewis basic organocatalysts, see: (a) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2003, 167 and references therein.
    • (2003) J. Am. Chem. Soc. , vol.167
    • Denmark, S.E.1    Fu, J.2
  • 20
    • 0037165679 scopus 로고    scopus 로고
    • For the use of chiral N-oxides as catalysts or promoters in other reactions, see: (a) Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2002, 124, 4233.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 4233
    • Denmark, S.E.1    Fan, Y.2
  • 25
    • 33644532366 scopus 로고    scopus 로고
    • note
    • Reports appeared while this work was being completed that confirmed the validity of this approach: see ref 5i and 51.
  • 26
    • 22844435241 scopus 로고
    • For a review on the allylation of aldehydes with ally(trichloro)silane, see: Hosomi, A. Acc. Chem. Res. 1988, 21, 2090.
    • (1988) Acc. Chem. Res. , vol.21 , pp. 2090
    • Hosomi, A.1
  • 28
    • 33644553985 scopus 로고    scopus 로고
    • note
    • The use of other solvents (toluene, dichloromethane, dichloroethane, THF, DME) led to lower yields and ee. The best result (25% yield, 42% ee) was observed in dichloromethane.
  • 29
    • 33644558191 scopus 로고    scopus 로고
    • note
    • It must be noted that both 10 and 11 are less sterically hindered and, hence, are likely to be better catalysts than 5b because they can have a stronger N-oxide/silicon interaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.