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Volumn , Issue 30, 2008, Pages 3528-3530

Tandem multi-step synthesis of C-carboxyazlactones promoted by N-heterocyclic carbenes

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; C CARBOXYAZLACTONE; CARBENE; LACTONE DERIVATIVE;

EID: 47949116057     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b806816j     Document Type: Article
Times cited : (45)

References (43)
  • 33
    • 47949101980 scopus 로고    scopus 로고
    • For related tandem protocols involving stoichiometric DMAP promoted catalysis see
    • A. R. Bharadwaj K. A. Scheidt Org. Lett. 2004 6 1465
    • (2004) Org. Lett. , vol.6 , pp. 1465
    • Bharadwaj, A.R.1    Scheidt, K.A.2
  • 36
    • 38849206288 scopus 로고    scopus 로고
    • Attempted use of KHMDS as a base to promote the two-step tandem formation of (±)- 7 from azlactone 4 (1 equiv.) using salt 5 (10 mol%), KHMDS (1.1 equiv.) and PhOCOCl (1.3 equiv.) in THF at rt gave only ∼40% conversion to (±)- 7
    • G. Peris E. Vedejs J. Org. Chem. 2008 73 1158
    • (2008) J. Org. Chem. , vol.73 , pp. 1158
    • Peris, G.1    Vedejs, E.2
  • 37
    • 1842502863 scopus 로고    scopus 로고
    • 3 in THF at rt, giving carbamate 8 in 68% isolated yield. See supporting information for full details In each case, the crude reaction product also contained 10-20% of carbamate 8
    • T. L. Amyes S. T. Diver J. P. Richard F. M. Rivas K. Toth J. Am. Chem. Soc. 2004 126 4366
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 4366
    • Amyes, T.L.1    Diver, S.T.2    Richard, J.P.3    Rivas, F.M.4    Toth, K.5
  • 43
    • 47949090515 scopus 로고    scopus 로고
    • 3 returned only starting material Fries type rearrangement was not observed in this reaction sequence. Furthermore, treatment of diphenyl carbonate with NHC 14 (9 mol%) derived from salt 5 (10 mol%) and KHMDS (9 mol%) returned only starting material after prolonged reaction times or upon heating
    • 3 returned only starting material


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.