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Volumn 10, Issue 7, 2008, Pages 1501-1504

Epoxy-annulations by reactions of α-amido ketones with vinyl sulfonium salts. Reagent versus substrate control and kinetic resolution

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; INORGANIC SALT; KETONE; PYRROLIDINE DERIVATIVE; SULFONIUM DERIVATIVE; VINYL DERIVATIVE;

EID: 45849090413     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800318h     Document Type: Article
Times cited : (67)

References (27)
  • 2
    • 0033609940 scopus 로고    scopus 로고
    • and references therein. For other applications of diphenyl vinyl sulfonium salts in the synthesis of heterocycles, see: b
    • For other applications of diphenyl vinyl sulfonium salts in the synthesis of heterocycles, see: (b) Wang, Y.; Zhang, W.; Colandrea, V. J.; Jimenez, L. S. Tetrahedron 1999, 55, 10659 and references therein.
    • (1999) Tetrahedron , vol.55 , pp. 10659
    • Wang, Y.1    Zhang, W.2    Colandrea, V.J.3    Jimenez, L.S.4
  • 3
    • 0035826644 scopus 로고    scopus 로고
    • For other work describing the use of chiral vinyl sulfonium salts in synthesis, see: c
    • For other work describing the use of chiral vinyl sulfonium salts in synthesis, see: (c) Kim, K.; Jimenez, L. S. Tetrahedron: Asymmetry 2001, 12, 999.
    • (2001) Tetrahedron: Asymmetry , vol.12 , pp. 999
    • Kim, K.1    Jimenez, L.S.2
  • 4
    • 33750488744 scopus 로고    scopus 로고
    • For the synthesis of the chiral sulfide from which 2 is derived, see: (a) Aggarwal, V. K.; Fang, G.; Kokotos, C. G.; Richardson, J.; Unthank, M. G. Tetrahedron 2006, 62, 11297.
    • For the synthesis of the chiral sulfide from which 2 is derived, see: (a) Aggarwal, V. K.; Fang, G.; Kokotos, C. G.; Richardson, J.; Unthank, M. G. Tetrahedron 2006, 62, 11297.
  • 6
    • 0042510063 scopus 로고    scopus 로고
    • For the synthesis of N-tosyl alanine, see: (a) Sdira, S. B.; Felix, C. P.; Giudicelli, M-B. A.; Seigle-Ferrand, P. F.; Perrin, M.; Lamartine, R. J. J. Org. Chem. 2003, 68, 6632.
    • For the synthesis of N-tosyl alanine, see: (a) Sdira, S. B.; Felix, C. P.; Giudicelli, M-B. A.; Seigle-Ferrand, P. F.; Perrin, M.; Lamartine, R. J. J. Org. Chem. 2003, 68, 6632.
  • 7
    • 59849120682 scopus 로고    scopus 로고
    • For the synthesis of amino-ketones from their respective Weinreb amides, see: b
    • For the synthesis of amino-ketones from their respective Weinreb amides, see: (b) Chen, W. B.; Jin, G. Y. Heteroatom Chem. 2003, 14, 603.
    • (2003) Heteroatom Chem , vol.14 , pp. 603
    • Chen, W.B.1    Jin, G.Y.2
  • 9
    • 59849096406 scopus 로고    scopus 로고
    • See Supporting Information for full details
    • See Supporting Information for full details.
  • 10
    • 59849096888 scopus 로고    scopus 로고
    • Reaction of the amino aldehyde (±)-6 was only carried out on the racemate. This example was done to establish the relationship between the size of the carbonyl substituent and level of substrate control. As both yield and diastereoselectivity were low with this substrate, further work on the enantioenriched material was not conducted.
    • Reaction of the amino aldehyde (±)-6 was only carried out on the racemate. This example was done to establish the relationship between the size of the carbonyl substituent and level of substrate control. As both yield and diastereoselectivity were low with this substrate, further work on the enantioenriched material was not conducted.
  • 12
    • 11844286876 scopus 로고    scopus 로고
    • For examples of epoxidation of unsaturated chiral 5-membered heterocycles to give anti-isomers see: (a) Quibbel, M, Ben, A, Flinn, N, Monk, T, Ramjee, M, Ray, P, Wang, Y, Watts, J. Bioorg. Med. Chem. 2005, 13, 609
    • For examples of epoxidation of unsaturated chiral 5-membered heterocycles to give anti-isomers see: (a) Quibbel, M.; Ben, A.; Flinn, N.; Monk, T.; Ramjee, M.; Ray, P.; Wang, Y.; Watts, J. Bioorg. Med. Chem. 2005, 13, 609.
  • 19
    • 59849110916 scopus 로고    scopus 로고
    • Only the higher yielding chiral ketone substrates were chosen to react with the valuable chiral vinyl sulfonium salt 2. The amino-aldehyde 6 was considered unsuitable for these reactions due to its lack of substrate-controlled diastereosectivity with diphenyl vinyl sulfonium salt 1
    • Only the higher yielding chiral ketone substrates were chosen to react with the valuable chiral vinyl sulfonium salt 2. The amino-aldehyde 6 was considered unsuitable for these reactions due to its lack of substrate-controlled diastereosectivity with diphenyl vinyl sulfonium salt 1.
  • 25
    • 59849120682 scopus 로고    scopus 로고
    • For the temperature-controlled treatment of the Weinreb amides with PhMgBr, see c
    • For the temperature-controlled treatment of the Weinreb amides with PhMgBr, see (c) Chen, W. B.; Jin, G. Y.; Heteroatom Chem. 2003, 14, 603.
    • (2003) Heteroatom Chem , vol.14 , pp. 603
    • Chen, W.B.1    Jin, G.Y.2
  • 26
    • 59849099722 scopus 로고    scopus 로고
    • For other examples of reactions of chiral sulfur ylides with chiral aldehydes, see a
    • For other examples of reactions of chiral sulfur ylides with chiral aldehydes, see (a) Aggarwal, V. K.; Bi, J. Beilstein J. Org. Chem. 2005, http://bjoc.beilstein-journals.org/content/1/1/4.
    • (2005) Beilstein J. Org. Chem
    • Aggarwal, V.K.1    Bi, J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.