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Volumn 54, Issue 1, 2015, Pages 227-230

Asymmetric synthesis of 2,3-dihydropyrroles by ring-opening/ cyclization of cyclopropyl ketones using primary amines

Author keywords

Cyclization; Kinetic resolution; N,N' dioxides; Ring opening; Scandium

Indexed keywords

AMINES; CHEMICAL COMPOUNDS; KETONES; KINETICS; SCANDIUM; SYNTHESIS (CHEMICAL);

EID: 84920090127     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201407880     Document Type: Article
Times cited : (121)

References (79)
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    • For selected examples of asymmetric syntheses of 2,5-dihydropyrroles, see
    • For selected examples of asymmetric syntheses of 2,5-dihydropyrroles, see:
  • 27
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    • For representative reviews, see
    • For representative reviews, see:
  • 35
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    • For selected examples of [3+2] annulations with enol silyl ethers, see
    • For selected examples of [3+2] annulations with enol silyl ethers, see:
  • 39
    • 84901402142 scopus 로고    scopus 로고
    • for such transformations with aldehydes, see
    • c) H. Xu, J. P. Qu, S. H. Liao, H. Xiong, Y. Tang, Angew. Chem. 2013, 125, 4096-4099; for such transformations with aldehydes, see:
    • (2013) Angew. Chem. , vol.125 , pp. 4096-4099
    • Xu, H.1    Qu, J.P.2    Liao, S.H.3    Xiong, H.4    Tang, Y.5
  • 50
    • 85081845541 scopus 로고    scopus 로고
    • For selected examples of [3+3] annulations with aromatic azomethine imines, see
    • For selected examples of [3+3] annulations with aromatic azomethine imines, see:
  • 55
    • 0041806585 scopus 로고    scopus 로고
    • c) I. S. Young, M. A. Kerr, Angew. Chem. Int. Ed. 2003, 42, 3023 - 3026; Angew. Chem. 2003, 115, 3131-3134;
    • (2003) Angew. Chem. , vol.115 , pp. 3131-3134
    • Young, I.S.1    Kerr, M.A.2
  • 62
    • 85081856574 scopus 로고    scopus 로고
    • For selected examples of ring-opening reactions with indoles, see
    • For selected examples of ring-opening reactions with indoles, see:
  • 64
    • 84877888233 scopus 로고    scopus 로고
    • for such transformations with amines, see
    • b) S. M. Wales, M. M. Walker, J. S. Johnson, Org. Lett. 2013, 15, 2558-2561; for such transformations with amines, see:
    • (2013) Org. Lett. , vol.15 , pp. 2558-2561
    • Wales, S.M.1    Walker, M.M.2    Johnson, J.S.3
  • 77
    • 85081852601 scopus 로고    scopus 로고
    • Using ScCl3.6H2O as the metal salt instead of Sc(OTf)3 and no LiCl resulted in similar outcomes (65% yield, 95% ee). Thus, LiCl acts as a promoter for counterion exchange
    • 3 and no LiCl resulted in similar outcomes (65% yield, 95% ee). Thus, LiCl acts as a promoter for counterion exchange.
  • 78
    • 85081854570 scopus 로고    scopus 로고
    • The absolute configuration of the recovered 1a was determined by comparing the circular-dichroism spectrum with that of 1i. CCDC 1013667 (3af) and CCDC 1013674 (1i) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • The absolute configuration of the recovered 1a was determined by comparing the circular-dichroism spectrum with that of 1i. CCDC 1013667 (3af) and CCDC 1013674 (1i) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.