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Volumn 71, Issue 13, 2006, Pages 5023-5026

Gold-catalyzed synthesis of alkylidene 2-oxazolidinones and 1,3-oxazin-2-ones

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CATALYST ACTIVITY; GOLD; POSITIVE IONS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 33745450775     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060520y     Document Type: Article
Times cited : (144)

References (56)
  • 1
    • 0038468227 scopus 로고    scopus 로고
    • For some reviews on oxazolidinones in asymmetric synthesis, see: (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-876.
    • (1996) Chem. Rev. , vol.96 , pp. 835-876
    • Ager, D.J.1    Prakash, I.2    Schaad, D.R.3
  • 6
    • 0035924978 scopus 로고    scopus 로고
    • and references therein
    • For biological interest of 1,3-amino alcohols, see: (c) Benedetti, F.; Norbedo, S. Chem. Commun. 2001, 203-204 and references therein.
    • (2001) Chem. Commun. , pp. 203-204
    • Benedetti, F.1    Norbedo, S.2
  • 23
    • 18044386806 scopus 로고    scopus 로고
    • For recent reviews on the metal-mediated electrophilic activation of alkynes, see: (a) Bruneau, C. Angew. Chem., Int. Ed. 2005, 44, 2328-2334.
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 2328-2334
    • Bruneau, C.1
  • 28
    • 27744595601 scopus 로고    scopus 로고
    • For recent reviews on gold-catalyzed reactions, see: (a) Hashmi, A. S. K. Angew. Chem., Int. Ed. 2005, 44, 6990-6993.
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 6990-6993
    • Hashmi, A.S.K.1
  • 45
    • 32644446865 scopus 로고    scopus 로고
    • During the preparation of this manuscript, the Au(I)-catalyzed cyclization of alkynyl tert-butyl carbonates has been reported: (a) Buzas, A.; Gagosz, F. Org. Lett. 2006, 3, 515-518.
    • (2006) Org. Lett. , vol.3 , pp. 515-518
    • Buzas, A.1    Gagosz, F.2
  • 47
    • 33745451902 scopus 로고    scopus 로고
    • note
    • Substrate 1 was prepared in 91% yield by the reaction of N-Boc-p-anisidine with propargyl bromide. See Supporting Information for details.
  • 48
    • 33244465401 scopus 로고    scopus 로고
    • 3Cl and silver salts, see for instance: ref 8b,c,e,f. See also: Zhang, J.; Yang, C.-G.; He, C. J. Am. Chem. Soc. 2006, 128, 1798-1799.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 1798-1799
    • Zhang, J.1    Yang, C.-G.2    He, C.3
  • 49
    • 33745456229 scopus 로고    scopus 로고
    • note
    • 6 alone as catalyst provided the cyclization product 2 but with only 73% of conversion after 24 h.
  • 50
    • 33745435454 scopus 로고    scopus 로고
    • note
    • The stereochemistry was assigned in the case of oxazolidinone 6 by a NOESY experiment (a strong cross-peak was observed between the olefinic proton and the allylic protons).
  • 51
    • 33745452406 scopus 로고    scopus 로고
    • note
    • For gold-catalyzed addition of alcohols to alkynes, see ref 10b,c.
  • 52
    • 33745477679 scopus 로고    scopus 로고
    • note
    • 2 (2 h) afforded a 35:65 mixture of the oxazolidinone 26 and its tert-butyl ether. These compounds were isolated in 28 and 59% yields after silica gel chromatography. (Diagram presented).
  • 54
    • 20844431887 scopus 로고    scopus 로고
    • For other processes with the N-Boc group acting as nucleophile in cyclization reactions, see for instance: (a) Hanessian, S.; Tremblay, M.; Marzi, M.; Del Valle, J. R. J. Org. Chem. 2005, 70, 5070-5085.
    • (2005) J. Org. Chem. , vol.70 , pp. 5070-5085
    • Hanessian, S.1    Tremblay, M.2    Marzi, M.3    Del Valle, J.R.4
  • 56
    • 33745463719 scopus 로고    scopus 로고
    • note
    • 2 at room temperature, cyclic products were not detected at all and only partial or complete N-Boc deprotection was observed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.