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Volumn 40, Issue 50, 1999, Pages 8827-8831

Efficient synthesis of various atropisomeric amides in optically pure forms and their application to asymmetric reactions

Author keywords

Anilides; Asymmetric reaction; Atropisomerism; Resolution

Indexed keywords

AMIDE; ANILINE DERIVATIVE; CARBONYL DERIVATIVE; LACTONE DERIVATIVE; ORGANOLITHIUM COMPOUND; OXALIC ACID DERIVATIVE; PANTOLACTONE;

EID: 0033544759     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01853-5     Document Type: Article
Times cited : (58)

References (27)
  • 8
    • 0002745259 scopus 로고    scopus 로고
    • Recently, Simpkins et al. also reported the synthesis of optically active N-(ortho-tert-butylphenyl)propanamide (93% ee) in accordance with our optical resolution method (Ref.2 a,b). (a) Hughes, A. D.; Simpkins, N. S. Synlett 1998, 967-968.
    • (1998) Synlett , pp. 967-968
    • Hughes, A.D.1    Simpkins, N.S.2
  • 9
    • 0031438042 scopus 로고    scopus 로고
    • On the other hand, the synthesis of optically pure forms of atropisomeric amides and imides through chromatographic optical resolution using chiral columns has been reported by two groups, while efforts to assign absolute configuration of these atropisomeric compounds have not yet been successful. (b) Curran, D. P.; Hale, G. R.; Geib, S. J.; Balog, A.; Cass, Q. B.; Degani, A. L. G.; Hernandes, M. Z.; Freitas, L. C. G. Tetrahedron: Asymmetry 1997, 8, 3955-3975.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 3955-3975
    • Curran, D.P.1    Hale, G.R.2    Geib, S.J.3    Balog, A.4    Cass, Q.B.5    Degani, A.L.G.6    Hernandes, M.Z.7    Freitas, L.C.G.8
  • 11
    • 85038149909 scopus 로고    scopus 로고
    • note
    • 3).
  • 12
    • 0013523168 scopus 로고
    • For recent examples of asymmetric addition reactions of organometallics to α-ketoamides and α-ketoesters possessing a chiral auxiliary, see: (a) Boireau, G.; Deberly, A.; Abenheim, D. Tetrahedron Lett. 1985, 26, 4181-4182.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 4181-4182
    • Boireau, G.1    Deberly, A.2    Abenheim, D.3
  • 17
    • 85038145848 scopus 로고    scopus 로고
    • It has been reported that the reaction of cycloalkylketoester, having chiral indanol derivative with PhMgBr, proceeded with excellent diastereoselectivity. See Ref. 5e
    • It has been reported that the reaction of cycloalkylketoester, having chiral indanol derivative with PhMgBr, proceeded with excellent diastereoselectivity. See Ref. 5e.
  • 27
    • 85038138255 scopus 로고    scopus 로고
    • note
    • 3).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.