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Volumn 73, Issue 4, 2008, Pages 1435-1439

Rh-catalyzed formation of dioxolanes from α-alkyl diazoesters: Diastereoselective cycloadditions of carbonyl ylides with selectivity over β-hydride elimination

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; CYCLOADDITION; RHODIUM; STEREOSELECTIVITY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 39349086608     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702308f     Document Type: Article
Times cited : (54)

References (36)
  • 1
    • 0000936734 scopus 로고
    • Reviews on carbonyl ylide cycloadditions: a
    • Reviews on carbonyl ylide cycloadditions: (a) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263.
    • (1991) Chem. Rev , vol.91 , pp. 263
    • Padwa, A.1    Hornbuckle, S.F.2
  • 12
    • 0037182699 scopus 로고    scopus 로고
    • For an elegant approach to controlling diastereoselective reactions of carbonyl ylides with a pendant Co-cluster, see: (i) Skaggs, A. J, Lin, E. Y, Jamison, T. F. Org. Lett. 2002, 4, 2277
    • For an elegant approach to controlling diastereoselective reactions of carbonyl ylides with a pendant Co-cluster, see: (i) Skaggs, A. J.; Lin, E. Y.; Jamison, T. F. Org. Lett. 2002, 4, 2277.
  • 13
    • 39349084044 scopus 로고    scopus 로고
    • 2b,12
    • 2b,12
  • 16
    • 0001031980 scopus 로고    scopus 로고
    • For the Rh-catalyzed preparation of (Z)-alkenes via β-hydride elimination, see: Taber, D. F.; Herr, R. J.; Pack, S. K.; Geremia, J. M. J. Org. Chem. 1996, 61, 2908 and references cited therein.
    • For the Rh-catalyzed preparation of (Z)-alkenes via β-hydride elimination, see: Taber, D. F.; Herr, R. J.; Pack, S. K.; Geremia, J. M. J. Org. Chem. 1996, 61, 2908 and references cited therein.
  • 17
    • 39349103006 scopus 로고    scopus 로고
    • 2c
    • 2c
  • 22
    • 33846113394 scopus 로고    scopus 로고
    • For other examples of Rh-catalyzed transformations that tolerate β-hydrogens, see refs 9 and 10
    • (a) Panne, P.; Fox, J. M. J. Am. Chem. Soc. 2007, 129, 22. For other examples of Rh-catalyzed transformations that tolerate β-hydrogens, see refs 9 and 10.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 22
    • Panne, P.1    Fox, J.M.2
  • 23
    • 27544502534 scopus 로고    scopus 로고
    • Hashimoto and co-workers had noted in enantioselective, intramolecular C-H insertions that higher selectivities over β-hydride elimination were obtained at -78°C: Minami, K.; Saito, H.; Tsutsui, H.; Nambu, H.; Anada, M.; Hashimoto, S. Adv. Synth. Catal. 2005, 347, 1483.
    • Hashimoto and co-workers had noted in enantioselective, intramolecular C-H insertions that higher selectivities over β-hydride elimination were obtained at -78°C: Minami, K.; Saito, H.; Tsutsui, H.; Nambu, H.; Anada, M.; Hashimoto, S. Adv. Synth. Catal. 2005, 347, 1483.
  • 24
    • 0028272257 scopus 로고    scopus 로고
    • 4: (a) Cox, G. G.; Haigh, D.; Hindley, R. M.; Miller, D. J.; Moody, C. J. Tetrahedron Lett. 1994, 35, 3139.
    • 4: (a) Cox, G. G.; Haigh, D.; Hindley, R. M.; Miller, D. J.; Moody, C. J. Tetrahedron Lett. 1994, 35, 3139.
  • 27
    • 1642501073 scopus 로고    scopus 로고
    • The stereochemistry of 6 was not assigned. For precedent for the formation of azines in Rh-catalyzed reactions of diazocompounds, see ref 10c and: (a) Petrukhina, M. A, Andreini, K. W, Walji, A. M, Davies, H. M. L. J. Chem. Soc, Dalton Trans. 2003, 4221
    • The stereochemistry of 6 was not assigned. For precedent for the formation of azines in Rh-catalyzed reactions of diazocompounds, see ref 10c and: (a) Petrukhina, M. A.; Andreini, K. W.; Walji, A. M.; Davies, H. M. L. J. Chem. Soc., Dalton Trans. 2003, 4221.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.