메뉴 건너뛰기




Volumn 75, Issue 4, 2010, Pages 1259-1265

Highly effective vinylogous Mukaiyama-Michael reaction catalyzed by silyl methide species generated from 1,1,3,3-tetrakis(trifluoromethanesulfonyl)propane

Author keywords

[No Author keywords available]

Indexed keywords

ACID CATALYST; BUTENOLIDES; CARBON ACID; CHEMICAL EQUATIONS; IN-SITU; MICHAEL REACTIONS; SYNTHETIC METHODOLOGY; TETRAKIS; UNSATURATED KETONES;

EID: 77249122498     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo902641g     Document Type: Article
Times cited : (48)

References (61)
  • 1
    • 45249121299 scopus 로고    scopus 로고
    • Yamamoto, H, Ishihara, K, Eds, Wiley-VCH: Weinheim, Germany
    • (a) Acid Catalysis in Modern Organic Synthesis; Yamamoto, H., Ishihara, K., Eds.; Wiley-VCH: Weinheim, Germany, 2008.
    • (2008) Acid Catalysis in Modern Organic Synthesis
  • 2
    • 47749122232 scopus 로고    scopus 로고
    • Berkessel, A, Groeger, H, Eds, Wiley-VCH: Weinheim, Germany
    • (b) Asymmetric Organocatalysis; Berkessel, A., Groeger, H., Eds.; Wiley-VCH: Weinheim, Germany, 2005;
    • (2005) Asymmetric Organocatalysis
  • 4
    • 84955366971 scopus 로고    scopus 로고
    • Silicon(IV) Lewis Acids
    • Yamamoto, H, Ed, Wiley-VCH: Weinheim, Germany
    • (a) Oishi, M. Silicon(IV) Lewis Acids. In Lewis Acids in Organic Synthesis; Yamamoto, H., Ed.; Wiley-VCH: Weinheim, Germany, 2000; Vol. 1, pp 355-393;
    • (2000) Lewis Acids in Organic Synthesis , vol.1 , pp. 355-393
    • Oishi, M.1
  • 5
    • 45249121299 scopus 로고    scopus 로고
    • Si(IV) Lewis acids
    • Yamamoto, H, Ishihara, K, Eds, Wiley-VCH: Weinheim, Germany
    • (b) Hosomi, A.; Miura, K. Si(IV) Lewis acids. In Acid Catalysis in Modern Organic Synthesis; Yamamoto, H., Ishihara, K., Eds.; Wiley-VCH: Weinheim, Germany, 2008; Vol. 1, pp 469-516.
    • (2008) Acid Catalysis in Modern Organic Synthesis , vol.1 , pp. 469-516
    • Hosomi, A.1    Miura, K.2
  • 6
    • 67651241741 scopus 로고    scopus 로고
    • (a) Takasu, K. Synlett 2009, 1905-1914.
    • (2009) Synlett , pp. 1905-1914
    • Takasu, K.1
  • 21
    • 0035813853 scopus 로고    scopus 로고
    • For examples of Brønsted acid catalysts equipped with an Tf 2CH group, see: (a) Ishihara, K, Hasegawa, A, Yamamoto, H. Angew. Chem, Int. Ed. 2001, 40, 4077-4079
    • 2CH group, see: (a) Ishihara, K.; Hasegawa, A.; Yamamoto, H. Angew. Chem., Int. Ed. 2001, 40, 4077-4079.
  • 24
    • 33746894125 scopus 로고    scopus 로고
    • 2CH group, see: Hasegawa, A.; Naganawa, Y.; Fushimi, M.; Ishihara, K.; Yamamoto, H. Org. Lett. 2006, 8, 3175-3178.
    • 2CH group, see: Hasegawa, A.; Naganawa, Y.; Fushimi, M.; Ishihara, K.; Yamamoto, H. Org. Lett. 2006, 8, 3175-3178.
  • 25
    • 33644537576 scopus 로고    scopus 로고
    • Boron and Silicon Enolates in Crossed Aldol Reaction
    • Mahrwald, R, Ed, Wiley-VCH: Weinheim, Germany
    • Mukaiyama, T.; Matsuo, J. Boron and Silicon Enolates in Crossed Aldol Reaction. In Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 1, pp 127-160.
    • (2004) Modern Aldol Reactions , vol.1 , pp. 127-160
    • Mukaiyama, T.1    Matsuo, J.2
  • 26
    • 77249153706 scopus 로고
    • Patent 2609148
    • (a) Nozari, M. S. Ger. Patent 2609148, 1976.
    • (1976)
    • Nozari, M.S.G.1
  • 27
    • 77249167714 scopus 로고
    • Patent 2609150
    • (b) Siefken, M. W. Ger. Patent 2609150, 1976.
    • (1976)
    • Siefken, M.W.G.1
  • 29
    • 77249163193 scopus 로고    scopus 로고
    • 2 is a nonfuming and nonhydroscopic crystal. This compound can be stored at room temperature for several months without decomposition.
    • 2 is a nonfuming and nonhydroscopic crystal. This compound can be stored at room temperature for several months without decomposition.
  • 31
    • 77249145908 scopus 로고    scopus 로고
    • Previously, in the field of polymer synthesis, carbon acid 1 had been used as a strong Brønsted acid catalyst, see: Robins, J.; Young, C. Ringopening polymerization. In ACS Symp. Ser. 1985, 286, 263-274.
    • Previously, in the field of polymer synthesis, carbon acid 1 had been used as a strong Brønsted acid catalyst, see: Robins, J.; Young, C. Ringopening polymerization. In ACS Symp. Ser. 1985, 286, 263-274.
  • 32
    • 67649452262 scopus 로고    scopus 로고
    • For selected examples of the VMM reactions with heterocyclic dienoxysilane, see: a
    • For selected examples of the VMM reactions with heterocyclic dienoxysilane, see: (a) Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G. Synlett 2009, 1525-1542.
    • (2009) Synlett , pp. 1525-1542
    • Casiraghi, G.1    Zanardi, F.2    Battistini, L.3    Rassu, G.4
  • 39
    • 0030781212 scopus 로고    scopus 로고
    • For enantioselective and diastereoselective 1,4-addition of silyloxyfurans catalyzed by chiral Lewis acids, see: (a) Kitajima, H.; Ito, K.; Katsuki, T. Tetrahedron 1997, 53, 17015-17028.
    • For enantioselective and diastereoselective 1,4-addition of silyloxyfurans catalyzed by chiral Lewis acids, see: (a) Kitajima, H.; Ito, K.; Katsuki, T. Tetrahedron 1997, 53, 17015-17028.
  • 44
    • 0037419866 scopus 로고    scopus 로고
    • For enantioselective and diastereoselective 1,4-addition of silyloxyfurans catalyzed by chiral organocatalyst, see
    • For enantioselective and diastereoselective 1,4-addition of silyloxyfurans catalyzed by chiral organocatalyst, see: Brown, S. P.; Goodwin,N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192-1194.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 1192-1194
    • Brown, S.P.1    Goodwin, N.C.2    MacMillan, D.W.C.3
  • 45
    • 17744381779 scopus 로고    scopus 로고
    • For the Lewis acid-catalyzed vinylogous Mukaiyama-aldol reaction with 3-bromo-2-silyloxyfuran, see: López, C. S.; Álvarez, R.; Vaz, B.; Faza, O. N.; de Lera, Á. R. J. Org. Chem. 2005, 70, 3654-3659.
    • For the Lewis acid-catalyzed vinylogous Mukaiyama-aldol reaction with 3-bromo-2-silyloxyfuran, see: López, C. S.; Álvarez, R.; Vaz, B.; Faza, O. N.; de Lera, Á. R. J. Org. Chem. 2005, 70, 3654-3659.
  • 46
    • 1542520958 scopus 로고    scopus 로고
    • In the presence of 1 mol, of 2,6-di-tert-butylpyridine, the VMM reaction of 2i was catalyzed by 1.0 mol%of carbon acid 1. This finding also supports that in situ generated silyl methide acts as a catalytically active species, see: Hollis, T. K, Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570-4581 and refs 4a and 6d
    • In the presence of 1 mol % of 2,6-di-tert-butylpyridine, the VMM reaction of 2i was catalyzed by 1.0 mol%of carbon acid 1. This finding also supports that in situ generated silyl methide acts as a catalytically active species, see: Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570-4581 and refs 4a and 6d.
  • 51
    • 0007835164 scopus 로고
    • For synthetic applications of α-bromo-γ-butenolides, see: a
    • For synthetic applications of α-bromo-γ-butenolides, see: (a) Takei, H.; Fukuda, Y.; Sugaya, K.; Taguchi, T.; Kawahara, T. Chem. Lett. 1980, 1307-1310.
    • (1980) Chem. Lett , pp. 1307-1310
    • Takei, H.1    Fukuda, Y.2    Sugaya, K.3    Taguchi, T.4    Kawahara, T.5
  • 56
    • 77249174815 scopus 로고    scopus 로고
    • Although it is possible that carbon acid 1 performs as a diprotic acid having two Tf2CH groups, the first proton dissociation constant Ka1 would play a central role in its acidity
    • a1 would play a central role in its acidity.
  • 59
    • 67650832095 scopus 로고    scopus 로고
    • 2 were recently revised, see: Leito, I.; Raamat, E.; Kutt, A.; Saame, J.; Kipper, K.; Koppel, I. A.; Koppel, I.; Zhang, M.; Mishima, M.; Yagupolskii, L. M.; Garlyauskayte, R. Y.; Filatov, A. A. J. Phys. Chem. A 2009, 113, 8421-8424.
    • 2 were recently revised, see: Leito, I.; Raamat, E.; Kutt, A.; Saame, J.; Kipper, K.; Koppel, I. A.; Koppel, I.; Zhang, M.; Mishima, M.; Yagupolskii, L. M.; Garlyauskayte, R. Y.; Filatov, A. A. J. Phys. Chem. A 2009, 113, 8421-8424.
  • 60
    • 77249153197 scopus 로고    scopus 로고
    • 13C NMR studies.
    • 13C NMR studies.
  • 61
    • 0347504883 scopus 로고    scopus 로고
    • 2 with allyltrimethylsilane, see: Hasegawa, A.; Ishihara, K.; Yamamoto, H. Angew. Chem., Int. Ed. 2003, 42, 5731-5733.
    • 2 with allyltrimethylsilane, see: Hasegawa, A.; Ishihara, K.; Yamamoto, H. Angew. Chem., Int. Ed. 2003, 42, 5731-5733.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.