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新型相转移催化剂的合成与催化性能研究 被引量：1

Studies on the Synthesis of Phase Transferred Catalysts and Their Application in Enantioselective Alkylation
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摘要 以金鸡纳生物碱和光学纯的联二萘酚为原料合成了一类新型手性相转移催化剂,并用于催化二苯甲酮亚胺甘氨酸叔丁酯的不对称烷基化反应中,得到了最高93%的产率和最高86%的对映选择性的烷基化产物. A novel class of chiral phase transfer catalysts was synthesized and identified. The new catalysts were further employed in enantioselective alkylation of N-（diphenylmethyene） glycine t-butyl ester with various alkyl halides in up to 93% yield and 86% ee.
作者 陈爱军 王振雷 刘全忠
机构地区 西华师范大学化学化工学院
出处 《西华师范大学学报（自然科学版）》 2008年第2期168-172,共5页 Journal of China West Normal University(Natural Sciences)
关键词 金鸡纳生物碱 联二萘酚 手性相转移催化剂 不对称烷基化 cinchona alkaloids binaphthol chiral phase transfer catalyst enantioselective alkylation
分类号 O626.1 [理学—有机化学]
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参考文献10

  • 1MIZUTA S, SHIBATA N, GOTO Y, et al. Cinchona Alkaloid-Catalyzed Enantioselective Monofluoromethylation Reaction Based on Fluorobis(phenylsulfonyl)Methane Chemistry Combined with a Mannich-Type Reaction [ J]. J. Am. Chem. Soc. ,2007, 129, 6394 - 6395.
  • 2MARUOKA K,OOI T, Enantioselective Amino Acid Synthesis by Chiral Phase-Transfer Catalysis [ J]. Chem. Rev. , 2003, 103, 3013-3028.
  • 3DOLLING U H, DAVIS P, GRABOWSKI E J J. Efficient Catalytic Asymmetric Alkylations Enantioselective Synthesis of ( + )- Indacrinone via Chiral Phase-Transfer Catalysis [J].J. Am. Chem. Soc. , 1984, 106, 446-447.
  • 4RAMACHANDRAN P V, MADHI S, BLAND-BERRY L, et al. Catalytic Enantioselective Synthesis of Glutamic Acid Derivatives via Tandem Conjugate Addition-Elimination of Activated AUylie Acetates Under Chiral PTC Conditions [ JJ. J. Am. Chem. Soc. , 2005, 127, 13450 - 13451.
  • 5OOI T, KAMEDA M, MARUOKA K. Molecular Design of a C2-Symmetric Chiral Phase-Transfer Catalyst for Practical Asymmetric Synthesis of-Amino Acids [J]. J. Am. Chem. Soc. ,1999, 121, 6519 -6520.
  • 6OOI T, KAMEDA M, MARUOKA K. Design of N-Spiro C2-Symmetric Chiral Quaternary Ammonium Bromides as Novel Chiral Phase-Transfer Catalysts: Synthesis and Application to Practical Asymmetric Synthesis of or-Amino Acids [ J ]. J. Am. Chem. Soc. , 2003, 125, 5139-5151.
  • 7OOI T,TAKEUCHI M,KATO D,et al. Highly Enantioselective Phase-Transfer-Catalyzed Alkylation of Protected -Amino Acid Amides Toward Practical Asymmetric Synthesis of Vicinal Diamines, -Amino Ketones, and -Amino Alcohols [ J ]. J. Am. Chem. Soe. , 2005, 127, 5073 - 5083.
  • 8LEE Y J, LEE J, KIM M J, et al. Highly Enantioselective Synthesis of (2S) - ( Hydroxymethyl)-Glutamic Acid by the Catalytic Michael Addition of 2 - Naphthalen-1 - yl-2-Oxazoline-4-Carboxylic Acid Tert-Butyl Ester [ J ]. Org. Lett. , 2005,7, 3207 - 3209.
  • 9OOI T,OHARA D,TAMURA M, et al. Design of New Chiral Phase-Transfer Catalysts with Dual Functions for Highly Enantioselective Epoxidation of ,β-Unsaturated Ketones [J]. J. Am. Chem. Soc. , 2004, 126, 6844 - 6845.
  • 10LIPPUR K,KANGER T,KRIIS K,et al. Synthesis of (2S,2'S)-Bimorpholine N, N '-Quaternary Dalts as Chiral Phase Transfer Catalysts [ J]. Tetrahedron : Asymmetry,2007, 18, 137 - 141.

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西华师范大学学报（自然科学版）
2008年 第2期

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