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Volumn 132, Issue 1, 2010, Pages 396-401

Enantioselective C-C bond formation by rhodium-catalyzed tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor carbenoids and allylic alcohols

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOLS; ALLYLIC ALCOHOL; C-C BOND FORMATION; CARBENOIDS; ENANTIOSELECTIVE; HIGH ENANTIOSELECTIVITY; HYDROXYCARBOXYLATE; O-H INSERTION; OXONIUM; QUATERNARY CENTERS; RHODIUM-CATALYZED; SIGMATROPIC REARRANGEMENTS; TWO-STEP PROCESS; YLIDE FORMATION;

EID: 74849096538     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9075293     Document Type: Article
Times cited : (96)

References (76)
  • 9
    • 0041878773 scopus 로고    scopus 로고
    • For leading reviews and latest references, see: a
    • For leading reviews and latest references, see: (a) Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861.
    • (2003) Chem. Rev , vol.103 , pp. 2861
    • Davies, H.M.L.1    Beckwith, R.E.J.2
  • 16
    • 33646034636 scopus 로고    scopus 로고
    • For references on enantioselective O-H insertion via copper-catalyzed decomposition of diazo carbonyl compounds, see: (a) Maier, T. C, Fu, G. C. J. Am. Chem. Soc. 2006, 128, 4594
    • For references on enantioselective O-H insertion via copper-catalyzed decomposition of diazo carbonyl compounds, see: (a) Maier, T. C.; Fu, G. C. J. Am. Chem. Soc. 2006, 128, 4594.
  • 19
    • 8344247661 scopus 로고    scopus 로고
    • For references on enantioselective N-H insertion via copper-catalyzed decomposition of diazo carbonyl compounds, see: (a) Bachmann, S, Fielenbach, D, Jørgensen, K. A. Org. Biomol. Chem. 2004, 2, 3044
    • For references on enantioselective N-H insertion via copper-catalyzed decomposition of diazo carbonyl compounds, see: (a) Bachmann, S.; Fielenbach, D.; Jørgensen, K. A. Org. Biomol. Chem. 2004, 2, 3044.
  • 22
    • 0027978020 scopus 로고    scopus 로고
    • Diastereoselective O-H and N-H insertions using dirhodium catalysis have been generally unsuccessful. For leading references see: (a) Aller, E, Cox, G. G, Miller, D. J, Moody, C. J. Tetrahedron Lett. 1994, 35, 5949
    • Diastereoselective O-H and N-H insertions using dirhodium catalysis have been generally unsuccessful. For leading references see: (a) Aller, E.; Cox, G. G.; Miller, D. J.; Moody, C. J. Tetrahedron Lett. 1994, 35, 5949.
  • 33
    • 45749136440 scopus 로고    scopus 로고
    • IV/BINOL as co-catalyst. For references, see: (a) Hu, W.; Xu, X.; Zhou, J.; Liu, W.-J.; Huang, H.; Hu, J.; Yang, L.; Gong, L.-Z. J. Am. Chem. Soc. 2008, 130, 7782.
    • IV/BINOL as co-catalyst. For references, see: (a) Hu, W.; Xu, X.; Zhou, J.; Liu, W.-J.; Huang, H.; Hu, J.; Yang, L.; Gong, L.-Z. J. Am. Chem. Soc. 2008, 130, 7782.
  • 38
    • 27544467423 scopus 로고    scopus 로고
    • A highly stereoselective [2,3]-sigmatropic rearrangement of sulfur ylide generated from aryldiazoacetate and allyl/propargyl sulfides was achieved with Cu(I) catalyst. For reference, see: Ma, M.; Peng, L.; Li, C.; Zhang, X.; Wang, J. J. Am. Chem. Soc. 2005, 127, 15016.
    • A highly stereoselective [2,3]-sigmatropic rearrangement of sulfur ylide generated from aryldiazoacetate and allyl/propargyl sulfides was achieved with Cu(I) catalyst. For reference, see: Ma, M.; Peng, L.; Li, C.; Zhang, X.; Wang, J. J. Am. Chem. Soc. 2005, 127, 15016.
  • 39
    • 0028805680 scopus 로고    scopus 로고
    • Studies from the Wood group have shown that the reaction of R-diazoketones with propargylic or allylic alcohols proceeds through enol intermediates, which subsequently undergo a Claisen rearrangement. For references, see: (a) Wood, J. L, Stoltz, B. M, Dietrich, H.-J. J. Am. Chem. Soc. 1995, 117, 10413
    • Studies from the Wood group have shown that the reaction of R-diazoketones with propargylic or allylic alcohols proceeds through enol intermediates, which subsequently undergo a Claisen rearrangement. For references, see: (a) Wood, J. L.; Stoltz, B. M.; Dietrich, H.-J. J. Am. Chem. Soc. 1995, 117, 10413.
  • 43
    • 0035914086 scopus 로고    scopus 로고
    • It would be reasonable to propose that a similar enol mechanism routinely occurs in rhodium-catalyzed O-H insertions, but for simple alcohols the enol intermediates tautomerize to the isolated keto products
    • (e) Drutu, I.; Krygowski, E. S.; Wood, J. L. J. Org. Chem. 2001, 66, 7025. It would be reasonable to propose that a similar enol mechanism routinely occurs in rhodium-catalyzed O-H insertions, but for simple alcohols the enol intermediates tautomerize to the isolated keto products.
    • (2001) J. Org. Chem , vol.66 , pp. 7025
    • Drutu, I.1    Krygowski, E.S.2    Wood, J.L.3
  • 45
    • 0032486807 scopus 로고    scopus 로고
    • 4-catalyzed reaction of cinnamyl methyl ether with ethyl diazoacetate results in ylide formation followed by a [2,3]-sigmatropic rearrangement with high asymmetric induction; see: Doyle, M. P.; Forbes, D. C.; Vasbinder, M. M.; Peterson, C. S. J. Am. Chem. Soc. 1998, 120, 7653.
    • 4-catalyzed reaction of cinnamyl methyl ether with ethyl diazoacetate results in ylide formation followed by a [2,3]-sigmatropic rearrangement with high asymmetric induction; see: Doyle, M. P.; Forbes, D. C.; Vasbinder, M. M.; Peterson, C. S. J. Am. Chem. Soc. 1998, 120, 7653.
  • 46
    • 57249093643 scopus 로고    scopus 로고
    • For reviews on the [2,3]-sigmatropic rearrangement of ylides, see: (a) Hodgson, D. M.; Pierard, F. Y. T. M.; Stupple, P. A. Chem. Soc. Rev. 2001, 30, 50.
    • For reviews on the [2,3]-sigmatropic rearrangement of ylides, see: (a) Hodgson, D. M.; Pierard, F. Y. T. M.; Stupple, P. A. Chem. Soc. Rev. 2001, 30, 50.
  • 48
    • 0000004354 scopus 로고    scopus 로고
    • For general references on the [2,3]-sigmatropic rearrangement of oxonium ylides formed by catalytic diazo decomposition, see: (a) Pirrung, M. C.; Werner, J. A. J. Am. Chem. Soc. 1986, 108, 6060.
    • For general references on the [2,3]-sigmatropic rearrangement of oxonium ylides formed by catalytic diazo decomposition, see: (a) Pirrung, M. C.; Werner, J. A. J. Am. Chem. Soc. 1986, 108, 6060.
  • 73
    • 74849133368 scopus 로고    scopus 로고
    • When 1 equiv of allyl alcohol 24e was used, the isolated yield of product 25e decreased to 32% but the enantioselectivity increased to 97% ee.
    • When 1 equiv of allyl alcohol 24e was used, the isolated yield of product 25e decreased to 32% but the enantioselectivity increased to 97% ee.
  • 75
    • 74849123391 scopus 로고    scopus 로고
    • The X-ray crystallographic data has been deposited in the Cambridge Crystallographic Database
    • The X-ray crystallographic data has been deposited in the Cambridge Crystallographic Database.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.