期刊文献+

修饰金鸡纳碱催化的不对称烯丙基烷基化反应

Asymmetric Allylic Alkylation Reaction by Modified Cincona Alkaloids-catalyzed
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摘要 以修饰金鸡纳碱的手性叔胺为催化剂,Morita-Baylis-Hillman碳酸酯与α-取代的β-酮酸酯经不对称烯丙基烷基化反应,以中等收率及较好的非对映选择性和对映选择性合成了一系列具有连续季碳叔碳手性中心的新型烷基取代β-酮酸酯类化合物,其结构经1H NMR和13C NMR表征。 Using modified cinchona alkaloid as the catalyst,a series of new compounds that bearing adjacent quaternary carbon and tertiary carbon chiral centers were synthesized by asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates with α-substituted β-ketoesters in moderated yield with excellent diastereoselectivities and good enantioselectivities.The structures were characterized by 1H NMR and 13C NMR.
作者 陈湜 董琳
出处 《合成化学》 CAS CSCD 北大核心 2012年第1期23-27,共5页 Chinese Journal of Synthetic Chemistry
基金 四川大学引进人才科研启动经费资助项目
关键词 金鸡纳碱 手性叔胺 不对称催化 Β-酮酸酯 烯丙基烷基化 合成 cincona alkaloid asymmetric organocatalysis allylic alkylation β-ketoesters synthesis
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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.
  • 4PENG Jing,CUI HaiLei & CHEN YingChun Key Laboratory of Drug-Targeting and Drug Delivery System,Ministry of Education,Department of Medicinal Chemistry,West China School of Pharmacy,Sichuan University,Chengdu 610041,China.Organocatalytic asymmetric allylic alkylation of sulfonylimidates with Morita-Baylis-Hillman carbonates[J].Science China Chemistry,2011,54(1):81-86. 被引量:1
  • 5Cui 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.
  • 6Peng J, Huang X, Chen Y C. Organocatalytic and electrophilic approach to oxindoles with C3-quaternary stereocenters [ J ]. Org Lett, 2010, 12 ( 19 ) : 4260 - 4263.
  • 7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
  • 8House H O, Hudson C B. Perhysro indan derivatives Ⅻ6-Methoxyindanone and its derivatives [ J]. J Org Chem, 1970,35 ( 8 ) : 647 - 651.
  • 9Jack K Crandall, Chrostian Pradat. Synthesis of Sulfones by phase-transfer alkylation of arenesulfinate salts[J]. J Org Chem,1985,50(8) :1327 - 1329.
  • 10Feng 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.

二级参考文献105

  • 1Bella M,Kobbelgaard S,Jorgensen K A. J. Am. Chem.Soc.,2005,127: 3670-3671.
  • 2Kobbelgaard S,Bella M,Jorgensen K A. J. Org. Chem.,2006,71: 4980-4987.
  • 3Alemán J,Richter B,Jorgensen K. A. Angew. Chem. Int.Ed.,2007,46: 5515-5519.
  • 4Wang X,Kitamura M,Maruoka K. J. Am. Chem. Soc.,2007,129: 1038-1039.
  • 5Bella M,Jrgensen K A. J. Am. Chem. Soc.,2004,126: 5672-5673.
  • 6Chen Z,Furutachi M,Kato Y,Matsunaga S,Shibasaki M.Angew. Chem. Int. Ed.,2009,48: 2218-2220.
  • 7Poulsen T B,Bernardi L,Bell M,Jrgensen K A. Angew.Chem. Int. Ed.,2006,45: 6551-6554.
  • 8Alemán J,Reyes E,Richter B,Overgaard J,Jrgensen K A. Chem. Commun.,2007,3921-3923.
  • 9Enders D,Grondal C,Hüttl M R M. Angew.Chem. Int. Ed.,2007,46: 1570-1581.
  • 10Halland N,Aburel P S,Jorgensen K A. Angew. Chem. Int.Ed.,2004,43: 1272-1277.

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