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Volumn 44, Issue 10, 2003, Pages 2145-2148

A quadruple ring-closing metathesis reaction in the synthesis of bis-spirocyclic compounds: Extending the scope of metathesis chemistry

Author keywords

Ring closing metathesis; Spirocycles

Indexed keywords

SPIRO COMPOUND;

EID: 0037416844     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00161-8     Document Type: Article
Times cited : (29)

References (44)
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    • For recent reviews of the metathesis reaction, see: (a) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371; (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413; (c) Tetrahedron symposium in print: Snapper, M. L.; Hoveyda, A. H. Eds.; 1999, 55, 8141; (d) Alkene Metathesis in Organic Synthesis; Top. Organomet. Chem. 1998, 1, Furstner, A. Ed.; (e) Blechert, S. Pure Appl. Chem. 1999, 8, 1393; (f) Furstner, A. Angew. Chem., Int. Ed. Engl. 2000, 39, 3012; (g) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
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    • For ring opening, double ring-closing strategies see, inter alia: (a) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634; (b) Zuercher, W. J.; Scholl, M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 4291; (c) Burke, S. D.; Quinn, K. J.; Chen, V. J. J. Org. Chem. 1998, 63, 8628; (d) Nicolaou, K. C.; Vega, J. A.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. Engl. 2001, 40, 4441.
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    • For ring opening, double ring-closing strategies see, inter alia: (a) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634; (b) Zuercher, W. J.; Scholl, M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 4291; (c) Burke, S. D.; Quinn, K. J.; Chen, V. J. J. Org. Chem. 1998, 63, 8628; (d) Nicolaou, K. C.; Vega, J. A.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. Engl. 2001, 40, 4441.
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    • For ring opening, double ring-closing strategies see, inter alia: (a) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634; (b) Zuercher, W. J.; Scholl, M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 4291; (c) Burke, S. D.; Quinn, K. J.; Chen, V. J. J. Org. Chem. 1998, 63, 8628; (d) Nicolaou, K. C.; Vega, J. A.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. Engl. 2001, 40, 4441.
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    • Burke, S.D.1    Quinn, K.J.2    Chen, V.J.3
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    • 0035803694 scopus 로고    scopus 로고
    • For ring opening, double ring-closing strategies see, inter alia: (a) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634; (b) Zuercher, W. J.; Scholl, M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 4291; (c) Burke, S. D.; Quinn, K. J.; Chen, V. J. J. Org. Chem. 1998, 63, 8628; (d) Nicolaou, K. C.; Vega, J. A.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. Engl. 2001, 40, 4441.
    • (2001) Angew. Chem., Int. Ed. Engl. , vol.40 , pp. 4441
    • Nicolaou, K.C.1    Vega, J.A.2    Vassilikogiannakis, G.3
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    • 0001354464 scopus 로고    scopus 로고
    • For tandem RCM reaction of dienynes see, inter alia: (a) Kim, S.-H.; Zuercher, W. J.; Bowden, N. B.; Grubbs, R. H. J. Org. Chem. 1996, 61, 1073; (b) Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem., Int. Ed. Engl. 2000, 39, 3101; (c) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648; (d) Boyer, F.-D.; Hanna, I. Tetrahedron Lett. 2002, 43, 7469.
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    • 0034283391 scopus 로고    scopus 로고
    • For tandem RCM reaction of dienynes see, inter alia: (a) Kim, S.-H.; Zuercher, W. J.; Bowden, N. B.; Grubbs, R. H. J. Org. Chem. 1996, 61, 1073; (b) Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem., Int. Ed. Engl. 2000, 39, 3101; (c) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648; (d) Boyer, F.-D.; Hanna, I. Tetrahedron Lett. 2002, 43, 7469.
    • (2000) Angew. Chem., Int. Ed. Engl. , vol.39 , pp. 3101
    • Renaud, J.1    Graf, C.-D.2    Oberer, L.3
  • 29
    • 0035930791 scopus 로고    scopus 로고
    • For tandem RCM reaction of dienynes see, inter alia: (a) Kim, S.-H.; Zuercher, W. J.; Bowden, N. B.; Grubbs, R. H. J. Org. Chem. 1996, 61, 1073; (b) Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem., Int. Ed. Engl. 2000, 39, 3101; (c) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648; (d) Boyer, F.-D.; Hanna, I. Tetrahedron Lett. 2002, 43, 7469.
    • (2001) Chem. Commun. , pp. 2648
    • Choi, T.-L.1    Grubbs, R.H.2
  • 30
    • 0037078394 scopus 로고    scopus 로고
    • For tandem RCM reaction of dienynes see, inter alia: (a) Kim, S.-H.; Zuercher, W. J.; Bowden, N. B.; Grubbs, R. H. J. Org. Chem. 1996, 61, 1073; (b) Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem., Int. Ed. Engl. 2000, 39, 3101; (c) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648; (d) Boyer, F.-D.; Hanna, I. Tetrahedron Lett. 2002, 43, 7469.
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  • 36
    • 85031229554 scopus 로고    scopus 로고
    • All new compounds gave satisfactory spectroscopic and HRMS or microanalytical data
    • All new compounds gave satisfactory spectroscopic and HRMS or microanalytical data.
  • 37
    • 85031218164 scopus 로고    scopus 로고
    • 6: C, 55.81; H, 7.02
    • 4Na (M+Na) 409.2355, found 409.2375.
  • 41
    • 85031222998 scopus 로고    scopus 로고
    • To a solution of octaene 3 (75 mg, 0.203 mmol) in dichloromethane (6.0 mL) was added catalyst 11 (18.0 mg, 0.02 mmol), the mixture was de-gassed and stirred for 3 h whereupon a further 10 mol% of catalyst was added and stirring continued for 24 h. Concentration and column chromatography (EtOAc:hexanes 1:1 increasing to EtOAc and then EtOAc:MeOH 4:1) afforded 10a (14.0 mg, 25%), 10b (19.5 mg, 35%) and 10c (14.0 mg, 24%)
    • 4Na (M+Na) 297.1103, found 297.1104.
  • 42
    • 85031234957 scopus 로고    scopus 로고
    • f value
    • f value.
  • 43
    • 85031224437 scopus 로고    scopus 로고
    • Modeling studies performed using PC Sparton Pro suggest dipole moments: 10a=0.53 debye, 10b=2.46 debye and 10c=4.26 debye. More rigorous molecular modeling studies are planned and will be presented in a full paper
    • Modeling studies performed using PC Sparton Pro suggest dipole moments: 10a=0.53 debye, 10b=2.46 debye and 10c=4.26 debye. More rigorous molecular modeling studies are planned and will be presented in a full paper.
  • 44
    • 85031216217 scopus 로고    scopus 로고
    • The rapid formation of five membered rings in RCM reactions has been noted before, see inter alia, Refs. 3a, 3c, 5a, 8c
    • The rapid formation of five membered rings in RCM reactions has been noted before, see inter alia, Refs. 3a, 3c, 5a, 8c.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.