Investigation of a novel diamine based chiral auxiliary in the asymmetric alkylation of ketones

被引:7
|
作者
Clarke, Sarah L.
McSweeney, Christina M.
McGlacken, Gerard P. [1 ]
机构
[1] Natl Univ Ireland Univ Coll Cork, Analyt & Biol Chem Res Facil, Cork, Ireland
基金
爱尔兰科学基金会;
关键词
IONOPHORE ANTIBIOTIC X-14547A; CYCLIC CARBAMATE HYDRAZONES; ALPHA-ALKYLATION; ACYCLIC KETONES; PROLINE; ALPHA; ALPHA-BISALKYLATION; TETRAHYDROPYRAN; DERIVATIVES; EFFICIENT;
D O I
10.1016/j.tetasy.2014.01.006
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A novel chiral auxiliary containing a pyrrolidine ring has been utilised in the preparation of various chiral ketones with good to excellent enantioselectivities (up to 92%). It has been successfully employed in aldol and Michael reactions giving moderate to high selectivity. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:356 / 361
页数:6
相关论文
共 50 条
  • [31] The synthesis of novel chiral aryloxazoline hydroaluminum and its asymmetric reduction for ketones
    Wu, HC
    Xu, DC
    Hua, WT
    ACTA CHIMICA SINICA, 2001, 59 (08) : 1340 - 1343
  • [32] Umpolung approach to the asymmetric α-alkylation of aldehydes and ketones
    Coltart, Don
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
  • [33] Catalytic Asymmetric Alkylation of Aryl Heteroaryl Ketones
    Ortiz, Pablo
    del Hoyo, Ana M.
    Harutyunyan, Syuzanna R.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (01) : 72 - 76
  • [34] Direct Asymmetric Alkylation of Ketones: Still Unconquered
    Cano, Rafael
    Zakarian, Armen
    McGlacken, Gerard P.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (32) : 9278 - 9290
  • [35] Asymmetric Alkylation of Ketones Catalyzed by Engineered TrpB
    Watkins-Dulaney, Ella J.
    Dunham, Noah P.
    Straathof, Sabine
    Turi, Soma
    Arnold, Frances H.
    Buller, Andrew R.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (39) : 21412 - 21417
  • [36] (S,S)-(+)-Pseudoephedrine as chiral auxiliary in asymmetric conjugate addition and tandem conjugate addition/α-alkylation reactions
    Reyes, Efraim
    Vicario, Jose L.
    Carrillo, Luisa
    Badia, Dolores
    Uria, Uxue
    Iza, Ainara
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (20): : 7763 - 7772
  • [37] Acylation, diastereoselective alkylation, and cleavage of an oxazolidinone chiral auxiliary - A multistep asymmetric synthesis experiment for advanced undergraduates
    Smith, Thomas E.
    Richardson, David P.
    Truran, George A.
    Belecki, Katherine
    Onishi, Megumi
    JOURNAL OF CHEMICAL EDUCATION, 2008, 85 (05) : 695 - 697
  • [38] DIASTEREOSELECTIVE ALKYLATION REACTIONS EMPLOYING A CAMPHOR-BASED CHIRAL OXAZINONE AUXILIARY
    AHN, KH
    LIM, AK
    LEE, SK
    TETRAHEDRON-ASYMMETRY, 1993, 4 (12) : 2435 - 2436
  • [39] Fine-Tuning the Structures of Chiral Diamine Ligands in the Catalytic Asymmetric Aldol Reactions of Trifluoromethyl Aromatic Ketones with Linear Aliphatic Ketones
    Zong, Hua
    Huang, Huayin
    Bian, Guangling
    Song, Ling
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (23): : 11768 - 11773
  • [40] Iridium Diamine Catalyst for the Asymmetric Transfer Hydrogenation of Ketones
    Vazquez-Villa, Henar
    Reber, Stefan
    Ariger, Martin A.
    Carreira, Erick M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (38) : 8979 - 8981