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Volumn 9, Issue 20, 2011, Pages 6899-6902

New synthesis of spirocycles by utilizing in situ forming hypervalent iodine species

Author keywords

[No Author keywords available]

Indexed keywords

ARYL ALKYNES; HYPERVALENT IODINE; IN-SITU FORMING; IODONIUM; SPIROCYCLIZATION;

EID: 80053320764     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c1ob06199b     Document Type: Article
Times cited : (87)

References (43)
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    • (2000) Alkaloide
    • Hesse, M.1
  • 27
    • 0025125762 scopus 로고
    • On the other hand, no general method using hypervalent iodine reagent to furnish carbon-carbon bonds toward alkynes was reported Reactions of alkenyliodonium salts with nucleophiles
    • T. Kitamura R. Furuki H. Taniguchi P. J. Stang Tetrahedron Lett. 1990 31 703
    • (1990) Tetrahedron Lett. , vol.31 , pp. 703
    • Kitamura, T.1    Furuki, R.2    Taniguchi, H.3    Stang, P.J.4
  • 30
    • 34547413951 scopus 로고    scopus 로고
    • Very recently, we reported the isolation of new iodonium salts formed by the spirocyclization, in which the possibility of a similar one-pot synthesis was described for specific cases. The utilization and optimization of the in situ generated hypervalent iodine species from iodoarenes were not treated in that study. See
    • J. Yan H. Jin Z. Chen J. Chem. Res. 2007 233
    • (2007) J. Chem. Res. , pp. 233
    • Yan, J.1    Jin, H.2    Chen, Z.3
  • 32
    • 77957846655 scopus 로고    scopus 로고
    • Other regioisomeric bis(iodoarene)s of 3h were less effective than the 2,2′-derivative in this transformation The fluoroalcohols can accelerate generation of hypervalent iodine(iii) species from iodoarenes and formation of the diaryliodonium salts. See
    • T. Dohi N. Takenaga K.-I. Fukushima T. Uchiyama D. Kato M. Shiro H. Fujioka Y. Kita Chem. Commun. 2010 46 7697
    • (2010) Chem. Commun. , vol.46 , pp. 7697
    • Dohi, T.1    Takenaga, N.2    Fukushima, K.-I.3    Uchiyama, T.4    Kato, D.5    Shiro, M.6    Fujioka, H.7    Kita, Y.8
  • 35
    • 77955471751 scopus 로고    scopus 로고
    • The use of excess amounts of the nucleophiles (∼5 equiv.) was possible in order to avoid introduction of mCPBA to the final spirocyclic products, though it was a very minor competitive path For selected examples of natural product syntheses containing the related ortho-spirolactone structures, see
    • T. Dohi N. Yamaoka Y. Kita Tetrahedron 2010 66 5775
    • (2010) Tetrahedron , vol.66 , pp. 5775
    • Dohi, T.1    Yamaoka, N.2    Kita, Y.3
  • 39
    • 0034597522 scopus 로고    scopus 로고
    • a values of conjugated acids of the nucleophiles are typically lower than 5 Comparable reaction yields were obtained for the substrates 1 in Table 1 in these nucleophiles
    • C. Cox S. J. Danishefsky Org. Lett. 2000 2 3493
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.