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Volumn 11, Issue 9, 2009, Pages 1919-1922

Sc(OTf)3-catalyzed conjugate allylation of alkylidene meldrum's acids

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EID: 66149097468     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9003959     Document Type: Article
Times cited : (26)

References (52)
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    • Selected recent examples: (a) Barker, T. J.; Jarvo, E. R. Org. Lett. 2009, 11, 1047-1049.
    • Selected recent examples: (a) Barker, T. J.; Jarvo, E. R. Org. Lett. 2009, 11, 1047-1049.
  • 5
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    • For a general review on reactions of allyl metal reagents, see
    • (e) Lou, S.; Moquist, P. N.; Schaus, S. E. J. Am. Chem. Soc. 2006, 128, 12660-12661. For a general review on reactions of allyl metal reagents, see:
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 12660-12661
    • Lou, S.1    Moquist, P.N.2    Schaus, S.E.3
  • 7
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    • Initial discovery using allylsilanes: (a) Hosomi, A.; Sakurai, H. J. Am. Chem. Soc. 1977, 99, 1673-1675. Allylstannanes:
    • Initial discovery using allylsilanes: (a) Hosomi, A.; Sakurai, H. J. Am. Chem. Soc. 1977, 99, 1673-1675. Allylstannanes:
  • 10
    • 35148881267 scopus 로고    scopus 로고
    • Conjugate allylation of nitroalkenes: (a) Shen, K.-H.; Liu, J.-T.; Wu, Y.-R.; Yao, C.-F. Synth. Commun. 2007, 37, 3677-3687.
    • Conjugate allylation of nitroalkenes: (a) Shen, K.-H.; Liu, J.-T.; Wu, Y.-R.; Yao, C.-F. Synth. Commun. 2007, 37, 3677-3687.
  • 19
    • 38649130639 scopus 로고    scopus 로고
    • For recent examples of 1,2-allylation of enals and enones using allyltin reagents, see: a
    • For recent examples of 1,2-allylation of enals and enones using allyltin reagents, see: (a) Zhang, T.; Shi, M.; Zhao, M. Tetrahedron 2008, 64, 2412-2418.
    • (2008) Tetrahedron , vol.64 , pp. 2412-2418
    • Zhang, T.1    Shi, M.2    Zhao, M.3
  • 23
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    • Conjugate allylation of cinnamaldehyde with allyllithium in the presence of a bulky aluminum phenoxide reagent has been reported: Ooi, T, Kondo, Y, Maruoka, K. Angew. Chem, Int. Ed. Engl. 1997, 36, 1183-1185
    • Conjugate allylation of cinnamaldehyde with allyllithium in the presence of a bulky aluminum phenoxide reagent has been reported: Ooi, T.; Kondo, Y.; Maruoka, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 1183-1185.
  • 24
    • 0142120599 scopus 로고    scopus 로고
    • Conjugate allylation of enones with catalytic indium and excess TMSCl: Lee, P. H.; Seomoon, D.; Kim, S.; Nagaiah, K.; Damle, S. V.; Lee, K. Synthesis 2003, 2189-2193.
    • Conjugate allylation of enones with catalytic indium and excess TMSCl: Lee, P. H.; Seomoon, D.; Kim, S.; Nagaiah, K.; Damle, S. V.; Lee, K. Synthesis 2003, 2189-2193.
  • 27
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    • Isolated examples of conjugate allylation in the presence of Lewis acids to alkylidene Meldrum's acids containing metallated dienes have been reported, see: a
    • Isolated examples of conjugate allylation in the presence of Lewis acids to alkylidene Meldrum's acids containing metallated dienes have been reported, see: (a) Wada, C. K.; Roush, W. R. Tetrahedron Lett. 1994, 35, 7351-7354.
    • (1994) Tetrahedron Lett , vol.35 , pp. 7351-7354
    • Wada, C.K.1    Roush, W.R.2
  • 31
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    • Alkylidene Meldrum's acids are significantly more electrophilic than the corresponding diethyl alkylidenemalonates, see
    • Alkylidene Meldrum's acids are significantly more electrophilic than the corresponding diethyl alkylidenemalonates, see: Kaumanns, O.; Mayr, H. J. Org. Chem. 2008, 73, 2738-2745.
    • (2008) J. Org. Chem , vol.73 , pp. 2738-2745
    • Kaumanns, O.1    Mayr, H.2
  • 32
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    • For transformations into arylketones, see: a
    • For transformations into arylketones, see: (a) Fillion, E.; Dumas, A. M. J. Org. Chem. 2008, 73, 2920-2923.
    • (2008) J. Org. Chem , vol.73 , pp. 2920-2923
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  • 36
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    • For reviews on transformations of Meldrum's acid derivatives, see: a
    • For reviews on transformations of Meldrum's acid derivatives, see: (a) Ivanov, A. S. Chem. Soc. Rev. 2008, 37, 789-811.
    • (2008) Chem. Soc. Rev , vol.37 , pp. 789-811
    • Ivanov, A.S.1
  • 41
    • 66149091078 scopus 로고    scopus 로고
    • The initial product formed by allylation is a triphenyltin enolate of Meldrum's acid that is protonated by acidic workup. See Supporting Information.
    • The initial product formed by allylation is a triphenyltin enolate of Meldrum's acid that is protonated by acidic workup. See Supporting Information.
  • 43
    • 0033550196 scopus 로고    scopus 로고
    • For other examples of diastereselective conjugate allylation not found in refs 2 and 3, see: a
    • For other examples of diastereselective conjugate allylation not found in refs 2 and 3, see: (a) Groaning, M. D.; Meyers, A. I. Tetrahedron Lett. 1999, 40, 8071-8074.
    • (1999) Tetrahedron Lett , vol.40 , pp. 8071-8074
    • Groaning, M.D.1    Meyers, A.I.2
  • 46
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    • For conjugate addition of indole to 1q and 1r formed in situ, see: (a) Boisbrun, M.; Kovács-Kulyassa, Á.; Jeannin, L.; Sapi, J.; Toupet, L.; Laronze, J.-Y. Tetrahedron Lett. 2000, 41, 9771-9775.
    • For conjugate addition of indole to 1q and 1r formed in situ, see: (a) Boisbrun, M.; Kovács-Kulyassa, Á.; Jeannin, L.; Sapi, J.; Toupet, L.; Laronze, J.-Y. Tetrahedron Lett. 2000, 41, 9771-9775.
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    • Relative stereochemistry was determined by analysis of coupling constants and proceeds with the same facial selectivity as the addition of indole ref 22
    • Relative stereochemistry was determined by analysis of coupling constants and proceeds with the same facial selectivity as the addition of indole (ref 22).
  • 51
    • 33845949270 scopus 로고    scopus 로고
    • Similar products have been obtained by the reaction of alkylidene Meldrum's acids with butadiene sulfone: Fillion, E.; Dumas, A. M.; Hogg, S. A. J. Org. Chem. 2006, 71, 9899-9902.
    • Similar products have been obtained by the reaction of alkylidene Meldrum's acids with butadiene sulfone: Fillion, E.; Dumas, A. M.; Hogg, S. A. J. Org. Chem. 2006, 71, 9899-9902.
  • 52
    • 66149090692 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.