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Volumn 45, Issue 9, 2006, Pages 1426-1429

Synthesis of functionalized cyclopentenes through catalytic asymmetric [3+2] cycloadditions of allenes with enones

Author keywords

Asymmetric synthesis; Cycloaddition; Homogeneous catalysis; Phosphanes

Indexed keywords

ASYMMETRIC SYNTHESIS; CYCLOADDITION; HOMOGENEOUS CATALYSIS; PHOSPHANES;

EID: 33745941049     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503312     Document Type: Article
Times cited : (342)

References (33)
  • 1
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    • 33746204463 scopus 로고    scopus 로고
    • (Eds.: D. F. Horrobin, M. S. Manku, P. Sirois, P. Borgeat), Churchill Livingston, Edinburgh
    • b) Prostaglandins: Prostaglandins, Leukotrienes and Essential Fatty Acids (Eds.: D. F. Horrobin, M. S. Manku, P. Sirois, P. Borgeat), Churchill Livingston, Edinburgh, 2002;
    • (2002) Prostaglandins, Leukotrienes and Essential Fatty Acids
  • 5
    • 0034829401 scopus 로고    scopus 로고
    • For recent examples of processes in which the asymmetry is introduced during the ring-forming reaction, see: a) H. M. L. Davies, B. Xiang, N. Kong, D. G. Stafford, J. Am. Chem. Soc. 2001, 123, 7461-7462;
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 7461-7462
    • Davies, H.M.L.1    Xiang, B.2    Kong, N.3    Stafford, D.G.4
  • 7
    • 0038665161 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 1800-1810.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1800-1810
  • 23
    • 4944250331 scopus 로고    scopus 로고
    • and references therein
    • Angew. Chem. Int. Ed. 2004, 43, 5066-5069, and references therein.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 5066-5069
  • 24
  • 25
    • 33746234923 scopus 로고    scopus 로고
    • note
    • 31P NMR spectroscopy, phosphepine 2 is the predominant phosphorus-containing species that is present during the [3+2] cycloaddition process. f) To the best of our knowledge, the stereochemistry of the enone is preserved in the cyclopentene.
  • 26
    • 33746187326 scopus 로고    scopus 로고
    • note
    • For non-asymmetric reactions, only maleates and fumarates have been shown to be suitable substrates. Lu et al. (e.g., ref. [4a]) and Zhang et al. (ref. [5]) were unable to achieve cycloadditions of other β-substituted α,β-unsaturated carbonyl compounds.
  • 27
    • 1842851813 scopus 로고    scopus 로고
    • For a recent discussion of the challenge of developing catalytic asymmetric methods for the synthesis of quaternary all-carbon centers, see: C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363-5367.
    • (2004) Proc. Natl. Acad. Sci. USA , vol.101 , pp. 5363-5367
    • Douglas, C.J.1    Overman, L.E.2
  • 28
    • 33746234924 scopus 로고    scopus 로고
    • note
    • Lu et al. have described phosphine-catalyzed [3+2] cycloadditions that generate spirocycles from enones that lack a β substituent (refs. [4d] and [4e]). They observe predominant formation of a different regioisomer (the two carbonyl groups are in a 1,3 relationship on the cyclopentene ring) from that depicted in Equation (4).
  • 30
    • 0037462129 scopus 로고    scopus 로고
    • For another recent example of a catalytic asymmetric method for the synthesis of spirocyclic compounds wherein an all-carbon quaternary stereocenter is established in the cyclization process, see: M. Hatano, K. Mikami, J. Am. Chem. Soc. 2003, 125, 4704-4705.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 4704-4705
    • Hatano, M.1    Mikami, K.2
  • 31
    • 33746248140 scopus 로고    scopus 로고
    • note
    • For the tetralone, a considerable quantity of unreacted starting material was observed. Increasing the amount of allene did not improve the yield.
  • 33
    • 33746187325 scopus 로고    scopus 로고
    • note
    • Molecular structures of phosphine catalysts given in Table 1: (Figure Presented)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.