메뉴 건너뛰기




Volumn 53, Issue 7, 2014, Pages 1915-1920

Ligand bite angle-dependent palladium-catalyzed cyclization of propargylic carbonates to 2-alkynyl azacycles or cyclic dienamides

Author keywords

alkynes; cyclization; nitrogen heterocycles; palladium; regioselectivity

Indexed keywords

ALKYNES; ANGLE-DEPENDENT; BIDENTATE PHOSPHINES; COMPUTATIONAL ANALYSIS; HIGH STEREOSELECTIVITIES; NITROGEN HETEROCYCLES; PALLADIUM-CATALYZED; REACTION PATHWAYS;

EID: 84893535448     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201309162     Document Type: Article
Times cited : (52)

References (50)
  • 20
    • 57749096199 scopus 로고    scopus 로고
    • et al., for recent asymmetric approaches to 2-alkynyl azacycles, see
    • K. L. Stevens, et al., Bioorg. Med. Chem. Lett. 2009, 19, 21; for recent asymmetric approaches to 2-alkynyl azacycles, see
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 21
    • Stevens, K.L.1
  • 26
    • 84893626744 scopus 로고    scopus 로고
    • The structures, including the absolute (and where appropriate, relative) configurations, of 5 a, 5 j, and 5 k were determined by single-crystal X-ray diffraction. Low-temperature single-crystal diffraction data were collected by using an Oxford Diffraction (Agilent) SuperNova, solved by using SIR92, and refined within the CRYSTALS suite. The Flack x parameter refined to 0.007(10), -0.002(12), and 0.00(1) for 5 a, 5 j, and 5 k, respectively. CCDC 965014, 965015, and 965016 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.
  • 40
    • 84866360071 scopus 로고    scopus 로고
    • Although the exact role of the carbonate leaving group in this catalytic process is unclear, with recent calculations suggesting an outer-sphere- coordination role, it (or methoxide) may at some point be involved in a proton-transfer step from the nucleophile to the allene.
    • Although the exact role of the carbonate leaving group in this catalytic process is unclear, with recent calculations suggesting an outer-sphere- coordination role (, J. O. C. Jiménez-Halla, M. Kalek, J. Stawinski, F. Himo, Chem. Eur. J. 2012, 18, 12424), it (or methoxide) may at some point be involved in a proton-transfer step from the nucleophile to the allene.
    • (2012) Chem. Eur. J. , vol.18 , pp. 12424
    • Jiménez-Halla, J.O.C.1    Kalek, M.2    Stawinski, J.3    Himo, F.4
  • 43
    • 0141633653 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 4215; for a review, see
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 4215
  • 44
    • 4544245050 scopus 로고    scopus 로고
    • S. Ma, Eur. J. Org. Chem. 2004, 1175; for related selectivity in the position of attack on an allenyl system, see Ref. [8c]; for a review of catalytic selective synthesis, see
    • (2004) Eur. J. Org. Chem. , pp. 1175
    • Ma, S.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.