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Volumn 9, Issue 11, 2007, Pages 2167-2170

Pt(II)-catalyzed synthesis of 1,2-dihydropyridines from aziridinyl propargylic esters

Author keywords

[No Author keywords available]

Indexed keywords

DIHYDROPYRIDINE DERIVATIVE; PLATINUM;

EID: 34250680552     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070658i     Document Type: Article
Times cited : (52)

References (27)
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    • For a review, see
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    • (1982) Chem. Rev , vol.82 , pp. 233-243
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    • Comins, D. L.; Hong, H.; Salvador, J. M. J. Org. Chem. 1991, 56, 7197-7199. See also ref 3.
    • Comins, D. L.; Hong, H.; Salvador, J. M. J. Org. Chem. 1991, 56, 7197-7199. See also ref 3.
  • 14
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    • For a discussion of pyran chemistry, see:, Katrizky, A. R, Rees, C. W, Eds, Pergamon: Oxford
    • For a discussion of pyran chemistry, see: Comprehensive Heterocyclic Chemistry; Katrizky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 3, pp 737-874.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.3 , pp. 737-874
  • 16
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    • We have recently described that other nitrogen nucleophiles (e.g, pyridinyl nitrogens) add faster to activated alkynes relative to the propargylic carboxylate. See: Smith, C. R, Bunnelle, E. M, Rhodes, A. J, Sarpong, R. Org. Lett. 2007, 9, 1169-1171
    • We have recently described that other nitrogen nucleophiles (e.g., pyridinyl nitrogens) add faster to activated alkynes relative to the propargylic carboxylate. See: Smith, C. R.; Bunnelle, E. M.; Rhodes, A. J.; Sarpong, R. Org. Lett. 2007, 9, 1169-1171.
  • 17
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    • For a recent discussion of vinyl aziridine rearrangements, see:, Yudin, A. K, Ed, WILEY-VCH: Weinheim
    • For a recent discussion of vinyl aziridine rearrangements, see: Ohno, H. In Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; WILEY-VCH: Weinheim, 2006; pp 37-72.
    • (2006) Aziridines and Epoxides in Organic Synthesis , pp. 37-72
    • Ohno, H.1
  • 18
    • 0035842303 scopus 로고    scopus 로고
    • A chelation-controlled 1,2-addition initially proposed to explain the high diastereoselectivity has recently been called into question. See: (a) Righi, G.; Piertrantonio, S.; Bonini, C. Tetrahedron 2001, 57, 10039-10046.
    • A chelation-controlled 1,2-addition initially proposed to explain the high diastereoselectivity has recently been called into question. See: (a) Righi, G.; Piertrantonio, S.; Bonini, C. Tetrahedron 2001, 57, 10039-10046.
  • 20
    • 34250639637 scopus 로고    scopus 로고
    • See Supporting Information for a detailed description for the synthesis of the substrates
    • See Supporting Information for a detailed description for the synthesis of the substrates.
  • 21
    • 28844460443 scopus 로고    scopus 로고
    • 2 has been used to catalyze the Overman rearrangement of trichloroacetimidates. See: Jaunzeme, I.; Jirgensons, A. Synlett 2005, 2984-2986.
    • 2 has been used to catalyze the Overman rearrangement of trichloroacetimidates. See: Jaunzeme, I.; Jirgensons, A. Synlett 2005, 2984-2986.
  • 23
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    • Mechanistically, this could proceed as illustrated below image presented
    • Mechanistically, this could proceed as illustrated below image presented.
  • 24
    • 34250634217 scopus 로고    scopus 로고
    • Crystallographic data have been deposited in the Cambridge Crystallographic Data Centre (CCDC #637309). Refinement data are provided in the Supporting Information.
    • Crystallographic data have been deposited in the Cambridge Crystallographic Data Centre (CCDC #637309). Refinement data are provided in the Supporting Information.
  • 25
    • 34250657166 scopus 로고    scopus 로고
    • The possibility of reduced stability of W-alkyl 1,2-dihydropyridines relative to N-tosyl or N-acyl 1,2-dihydropyridines under the reaction conditions may also contribute to the lack of success of this reaction.
    • The possibility of reduced stability of W-alkyl 1,2-dihydropyridines relative to N-tosyl or N-acyl 1,2-dihydropyridines under the reaction conditions may also contribute to the lack of success of this reaction.
  • 27
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    • Enantiopure la was obtained by preparative chiral column HPLC of the racemate. For more information, see the Supporting Information.
    • Enantiopure la was obtained by preparative chiral column HPLC of the racemate. For more information, see the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.