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Volumn 71, Issue 18, 2006, Pages 6991-6995

Palladium-catalyzed decarboxylative aza-Michael addition-allylation reactions between allyl carbamates and activated olefins. Generation of quaternary carbon adjacent to secondary amine carbon center

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CRYSTALLOGRAPHY; OLEFINS; PALLADIUM; STEREOCHEMISTRY;

EID: 33750479007     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061110c     Document Type: Article
Times cited : (53)

References (66)
  • 14
  • 16
    • 0003939992 scopus 로고
    • Graziani, M., Hubert, A. J., Noels, A. F., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands
    • (i) Fiaud, J. C. In Metal-Promoted Selectivity in Organic Synthesis; Graziani, M., Hubert, A. J., Noels, A. F., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1991.
    • (1991) Metal-Promoted Selectivity in Organic Synthesis
    • Fiaud, J.C.1
  • 39
  • 48
    • 0344877748 scopus 로고
    • The palladium-catalyzed intramolecular Michael addition of the ketone enolates generated by the decarboxylation of allyl β-keto carboxylates is known; see: Nokami, J.; Watanabe, H.; Mandai, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett. 1989, 30, 4829-4832.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 4829-4832
    • Nokami, J.1    Watanabe, H.2    Mandai, T.3    Kawada, M.4    Tsuji, J.5
  • 55
    • 33845554080 scopus 로고
    • 2Ph is difficult due to the steric repulsion of electron-withdrawing groups, although the small and linear cyano group leads to much less disruption than does the ester overlap. This phenomenon is in accord with Boeckman's and our previous results: see: (a) Boeckmann, R. K.; Ko, S. S. J. Am. Chem. Soc. 1982, 104, 1033.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 1033
    • Boeckmann, R.K.1    Ko, S.S.2
  • 56
    • 33750490499 scopus 로고    scopus 로고
    • note
    • (b) Ref 7. It was believed that in the case of cyclic enones coplanarity is maintained, and that may be the reason for their high reactivity.
  • 58
    • 33750433299 scopus 로고    scopus 로고
    • note
    • Efforts to determine the stereochemistry of 5n were undertaken using nOe experiment. However, no satisfactory results could be obtained. For X-ray crystallographic analysis data, see Supporting Information.
  • 59
    • 0032507933 scopus 로고    scopus 로고
    • Apart from the ability of the cyano group to undergo various structural manipulation depending on the reagents used, it can be used for various reactions: see: Liu, H.-J.; Zhu, J.-L.; Shia, K.-S. Tetrahedron Lett. 1998, 39, 4183-4186.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 4183-4186
    • Liu, H.-J.1    Zhu, J.-L.2    Shia, K.-S.3
  • 60
    • 0142062470 scopus 로고    scopus 로고
    • Since the carbamates are weak nucleophiles, Michael addition of them to enones generally needs the use of promoters; see: (a) Xu, L.-W.; Xia, C.-G.; Hu, X.-X. Chem. Commun. 2003, 2570-2571.
    • (2003) Chem. Commun. , pp. 2570-2571
    • Xu, L.-W.1    Xia, C.-G.2    Hu, X.-X.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.