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Volumn 65, Issue 10, 2000, Pages 3154-3159

Axially chiral analogues of 4-(dimethylamino)pyridine: Novel catalysts for nonenzymatic enantioselective acylations

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE;

EID: 0034685863     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0000574     Document Type: Article
Times cited : (170)

References (52)
  • 3
    • 0027160610 scopus 로고
    • and references therein
    • For KR of secondary alcohols with chiral acyl donors, see: Evans, D. A.; Anderson, J. C.; Taylor, M. K. Tetrahedron Lett. 1993, 34, 5563-5566 and references therein.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 5563-5566
    • Evans, D.A.1    Anderson, J.C.2    Taylor, M.K.3
  • 5
    • 0029876822 scopus 로고    scopus 로고
    • For nonenzymatic enantioselective acylation catalysts, see: (a) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809-1810.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1809-1810
    • Vedejs, E.1    Chen, X.2
  • 14
    • 0032486788 scopus 로고    scopus 로고
    • erratum, see p 10276
    • (j) Garrett, C. E.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 7479-7483 (erratum, see p 10276).
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 7479-7483
    • Garrett, C.E.1    Fu, G.C.2
  • 27
    • 0002244727 scopus 로고
    • For leading references on DMAP and its congeners, see: (a) Litvinenko, L. M.; Kirichenko, A. I. Dokl. Chem. (Engl. Transl.) 1967, 763-766 [Dokl. Akad. Nauk. SSSR 1967, 176, 97-100].
    • (1967) Dokl. Akad. Nauk. SSSR , vol.176 , pp. 97-100
  • 34
    • 0343869088 scopus 로고    scopus 로고
    • unpublished results. See also refs 5a,b
    • Spivey, A. C.; Maddaford, A., unpublished results. See also refs 5a,b.
    • Spivey, A.C.1    Maddaford, A.2
  • 35
    • 0342563440 scopus 로고    scopus 로고
    • note
    • s = (rate constant of fast-reacting enantiomer)/(rate constant of slow-reacting enantiomer).
  • 36
    • 0006983979 scopus 로고    scopus 로고
    • Cambridge Soft Corp.: U.S.
    • Computer program: CS Chem3D Pro, version 4.0; Cambridge Soft Corp.: U.S., 1997.
    • (1997) CS Chem3D Pro, Version 4.0
  • 39
    • 0343869086 scopus 로고    scopus 로고
    • note
    • Comparative atropisomerization kinetic studies for 3-aryl analogues of amine 1 and DMAP (ref 7b) indicated that biaryl 15 would be configurationally sufficiently stable at room temperature, enabling its optical resolution and convenient use in enantiopure form without any risk of racemization.
  • 43
    • 0343869085 scopus 로고    scopus 로고
    • note
    • 3 instead of NaOH as base gives the 5-bromo derivative of biaryl 12 in a 30% yield. Further functionalization of the 5-position can open access to a variety of novel catalyst candidates. Suzuki cross-coupling of aryl dibromide 11 with sterically less demanding arylboronic acids (i.e., 1-naphthalene-or 3-methoxybenzeneboronic acid) affords the products of bis-coupling in high yield (74% and 97%, respectively).
  • 46
    • 0343433362 scopus 로고    scopus 로고
    • note
    • 1 = Me], were not sufficiently soluble at -78° C for CKR to be carried out.
  • 47
    • 28844436100 scopus 로고
    • For KR of partially enriched compounds and "double" KR, see: (a) Horeau, A. Tetrahedron 1975, 31, 1307-1309.
    • (1975) Tetrahedron , vol.31 , pp. 1307-1309
    • Horeau, A.1
  • 50
    • 0342997720 scopus 로고    scopus 로고
    • note
    • 2O as acyl donor.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.