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Organocatalytic asymmetric allylic alkylation of sulfonylimidates with Morita-Baylis-Hillman carbonates 被引量:1

Organocatalytic asymmetric allylic alkylation of sulfonylimidates with Morita-Baylis-Hillman carbonates
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摘要 The asymmetric allylic alkylation reaction of sulfonylimidates with various Morita-Baylis-Hillman (MBH) carbonates was accomplished by the catalysis of commercially available cinchona alkaloids catalyst (DHQD)2AQN.The corresponding allylic alkylation products were obtained in good yields with high stereoselectivities (up to 99% ee,89:11 dr). The asymmetric allylic alkylation reaction of sulfonylimidates with various Morita-Baylis-Hillman (MBH) carbonates was accomplished by the catalysis of commercially available cinchona alkaloids catalyst (DHQD)2AQN.The corresponding allylic alkylation products were obtained in good yields with high stereoselectivities (up to 99% ee,89:11 dr).
出处 《Science China Chemistry》 SCIE EI CAS 2011年第1期81-86,共6页 中国科学(化学英文版)
基金 financially Supported by the National Natural Science Foundation of China (20772084)
关键词 烷基化反应 烯丙基 不对称 碳酸盐 有机催化 立体选择性 催化作用 碱催化剂 organocatalysis asymmetric allylic alkylation sulfonylimidates Morita-Baylis-Hillman carbonates cinchona alkaloids
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参考文献28

  • 1Feng X,Yuan YQ,Cui HL,Jiang K,Chen YC.Organocatalytic per- oxy-asymmetric allylic alkylation. Organic and Biomolecular Chemistry . 2009
  • 2Zhang SJ,Cui HL,Jiang K,Li R,Ding ZY,Chen YC.Enantioselec- tive allylic amination of Morita-Baylis-Hillman carbonates catalysed by modified cinchona alkaloids. European Journal of Organic Chemistry . 2009
  • 3Hu ZK,Cui HL,Jiang K,Chen YC.Enantioselective O-allylic alky- lation of Morita-Baylis-Hillman carbonates with oxime. Sci China Chem . 2010
  • 4Larsen JD,Bundgaard H.Prodrug forms for the sulfonamide group III chemical and enzymatic hydrolysis of various N-sulfonyl imidates-a novel prodrug form for a sulfonamide group or an ester function. International Journal of Pharmaceutics . 1989
  • 5Kupfer R,Nagel M,Würthwein EU,Allrnann R.Synthese und struktur von N-acylimidsaureestern. Chemische Berichte . 1985
  • 6Matsubara R,Berthiol F,Kobayashi S.Sulfonylimidates as nucleo- philes in catalytic addition reactions. Journal of the American Chemical Society . 2008
  • 7Matsubara R,Kobayashi S.DBU-catalyzed addition reactions of sul- fonylimidates. Synthesis . 2008
  • 8Kan SBJ,Matsubara R,Berthio F,Kobayashi S.Catalytic direct-type substitution reaction of α-alkyl enolates: A Pd/Br nsted base-catalysed approach to the decarboxylative allylation of sulfonylimidates. Chemical Communications . 2008
  • 9Nguyen HV,Matsubara R,Kobayashi S.Addition reactions of sul- fonylimidates with imines catalyzed by alkaline earth metals. Angewandte Chemie International Edition . 2009
  • 10Massa A,Utsumi N,Barbas III CF.N-tosylimidates in highly enanti- oselective organocatalytic michael reactions. Tetrahedron Letters . 2009

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  • 1Faye Maertens, Suzanne teppet, Frans compemolle. Incorporation of diarylbutylamine pharmacophore into indeno- or naphtho [ 1,2-b ] pyran Ring Systems [ J ]. Eur J Org Chem,2004:2707-2714.
  • 2Eugene G, Tamar Y, Alfred H. Utilization of ethyl 2-[(phenylsulfonyl) methyl ] acrylate for the synthesis of a-methylenevaIerolactones [ J ]. J Org Chem, 1990, 55 (24) :5977 -5982.
  • 3Carlos A M Fraga, Lis Helena P Teixeira, Carla Mafia de S Menezes, et al. Studies on diastereoselective re- duction of cyclic β-ketoesters with boron hydrides. Part 4:The reductive profile of functionalized cyclohexanone derivatives [ J ]. Tetrahedron,2004,60: 2745 - 2755.
  • 4Cui H L, Peng J, Chen Y C. etal. Dual organocatalysis : Asymmetric anylic-allylic alkylation of a, a-dicyanoalkenes and Morita-Baylis-Hilhnan carbonates [J].Chem Eur J,2009,15 : 1574 - 1577.
  • 5Peng J, Huang X, Chen Y C. Organocatalytic and electrophilic approach to oxindoles with C3-quaternary stereocenters [ J ]. Org Lett, 2010, 12 ( 19 ) : 4260 - 4263.
  • 6House H O, Hudson C B. Perhysro indan derivatives Ⅻ6-Methoxyindanone and its derivatives [ J]. J Org Chem, 1970,35 ( 8 ) : 647 - 651.
  • 7Jack K Crandall, Chrostian Pradat. Synthesis of Sulfones by phase-transfer alkylation of arenesulfinate salts[J]. J Org Chem,1985,50(8) :1327 - 1329.
  • 8Feng J, Lu X, Kong A, etal. A highly regio- and stero-selective [ 3 + 2 ] annulation of allylic com- pounds and 2-substituted 1,1-dicyanoalkenes through a catalytic carbo-phosphorus ylid reaction[ J ]. Tetra- hedron,2007,63:6035 - 6041.
  • 9D Y S, Hart X L, Lu X Y. Alkaloids-catalyzed regio- and enant/o-se]ectlve allylic nucleophilic substitution of tert-butyl carbonate of the Morit-Bayllc-Hillman products [ J ]. Tetrahedron Left, 2004, 45: 4967 - 4971.
  • 10方玲,石岩,朱成建.有机小分子催化的β-酮酯不对称α-官能化反应[J].化学进展,2010,22(9):1679-1686. 被引量:1

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