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Volumn 3, Issue 8, 2001, Pages 1129-1131

One-pot synthesis of enantiomerically enriched 2,3-disubstituted cyclopentanones via copper-catalyzed 1,4-reduction and alkylation

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENT; COPPER; CYCLOPENTANE DERIVATIVE; CYCLOPENTANONE;

EID: 0035912344     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015577f     Document Type: Article
Times cited : (74)

References (32)
  • 1
    • 85077870910 scopus 로고
    • For reviews on conjugate addition of organocuprates and enolate trapping, see: (a) Taylor, R. J. K. Synthesis 1985, 364.
    • (1985) Synthesis , pp. 364
    • Taylor, R.J.K.1
  • 2
    • 0000837820 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York
    • (b) Hulce, M.; Chapdelaine, M. J. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, p 237.
    • (1991) Comprehensive Organic Chemistry , vol.4 , pp. 237
    • Hulce, M.1    Chapdelaine, M.J.2
  • 9
    • 0035977640 scopus 로고    scopus 로고
    • During the preparation of this manuscript, an efficient conjugate addition system for cyclopentenones was reported, see: (c) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 755
    • Degrado, S.J.1    Mizutani, H.2    Hoveyda, A.H.3
  • 14
    • 0002782655 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York
    • (b) Caine, D. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, p 1.
    • (1991) Comprehensive Organic Chemistry , vol.3 , pp. 1
    • Caine, D.1
  • 18
    • 0039063421 scopus 로고
    • Often, α-substituents have been employed to prevent equilibration. For the use of arylhetero α-substituents as substrate auxiliaries, see: (a) Fang, J.-M. J. Org. Chem. 1982, 47, 3464.
    • (1982) J. Org. Chem. , vol.47 , pp. 3464
    • Fang, J.-M.1
  • 20
    • 0000634441 scopus 로고
    • Morrison, J. D., Ed.; Academic Press: New York, Chapter 8
    • (c) Posner, G. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vol. 2, Chapter 8.
    • (1983) Asymmetric Synthesis , vol.2
    • Posner, G.H.1
  • 21
    • 33845183574 scopus 로고
    • also see ref 7b
    • For monoalkylation of the lithium enolate of cyclopentanone in THF-HMPA solution using additives, see: Monta, Y.; Suzuki, M.; Noyori, R. J. Org. Chem. 1989, 54, 1785, also see ref 7b.
    • (1989) J. Org. Chem. , vol.54 , pp. 1785
    • Monta, Y.1    Suzuki, M.2    Noyori, R.3
  • 24
    • 0000040309 scopus 로고
    • Except these cases where tris(dialkylamino)sulfonium difluorotrimethylsilicate (TASF) was used as the fluoride source, see: (a) Noyori, R.; Nishida, I.; Sakata, J. Tetrahedron Lett. 1980, 21, 2085.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 2085
    • Noyori, R.1    Nishida, I.2    Sakata, J.3
  • 27
    • 0001443339 scopus 로고    scopus 로고
    • (b) Pilcher, A. S.; DeShong, P. J. Org. Chem. 1996, 61, 6901. For a revised synthetic procedure of analytically pure TBAT, see:
    • (1996) J. Org. Chem. , vol.61 , pp. 6901
    • Pilcher, A.S.1    DeShong, P.2
  • 29
    • 0042790189 scopus 로고    scopus 로고
    • note
    • (d) Commercial TBAT was treated with anhydrous benzene and dried under vacuum in order to remove possible water contamination (see Supporting Information).
  • 30
    • 0041788006 scopus 로고    scopus 로고
    • note
    • 5b


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.