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
来源：
TETRAHEDRON-ASYMMETRY | 2014年 / 25卷 / 04期
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
  • [41] Direct asymmetric syntheses of chiral aldehydes and ketones via N-acyl chiral auxiliary derivatives including chiral Weinreb amide equivalents
    Davies, Stephen G.
    Fletcher, Ai M.
    Thomson, James E.
    CHEMICAL COMMUNICATIONS, 2013, 49 (77) : 8586 - 8598
  • [42] ASYMMETRIC ALKYLATION OF ACYCLIC KETONES VIA CHIRAL METALLO ENAMINES - EFFECT OF KINETIC VS THERMODYNAMIC METALATIONS
    MEYERS, AI
    WILLIAMS, DR
    JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (16): : 3245 - 3247
  • [43] ASYMMETRIC SULFENYLATION OF KETONES WITH CHIRAL SULFENAMIDES
    HIROI, K
    NISHIDA, M
    NAKAYAMA, A
    NAKAZAWA, K
    FUJII, E
    SATO, S
    CHEMISTRY LETTERS, 1979, (08) : 969 - 972
  • [44] Asymmetric Epoxidation Catalyzed by Chiral Ketones
    Wong, Man Kin
    Yip, Yiu Chung
    Yang, Dan
    ASYMMETRIC CATALYSIS FROM A CHINESE PERSPECTIVE, 2011, 36 : 123 - 152
  • [45] ASYMMETRIC REDUCTION OF KETONES WITH CHIRAL LIMONYLBORANE
    KIM, JD
    KIM, JE
    CHA, JS
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1982, 3 (03) : 130 - 131
  • [46] ASYMMETRIC SYNTHESES VIA METALATED CHIRAL HYDRAZONES - OVERALL ENANTIOSELECTIVE ALPHA-ALKYLATION OF ACYCLIC KETONES
    ENDERS, D
    EICHENAUER, H
    BAUS, U
    SCHUBERT, H
    KREMER, KAM
    TETRAHEDRON, 1984, 40 (08) : 1345 - 1359
  • [47] Asymmetric photoreactions catalyzed by chiral ketones
    Bian, Bao-Ji
    Yang, Liu
    Qiao, Li-Xin
    Zhang, Qiang
    He, Wei
    RSC ADVANCES, 2025, 15 (04) : 2874 - 2889
  • [48] ASYMMETRIC REDUCTION OF PROCHIRAL HYDROXY KETONES WITH A CHIRAL REDUCING AGENT PREPARED FROM TIN(II) CHLORIDE, A CHIRAL DIAMINE, AND DIISOBUTYLALUMINUM HYDRIDE
    MUKAIYAMA, T
    TOMIMORI, K
    ORIYAMA, T
    CHEMISTRY LETTERS, 1985, (09) : 1359 - 1362
  • [49] Asymmetric hydrogenation of aromatic ketones catalyzed by chiral diamine modified Ru/γ-Al2O3
    Xiong, W
    Huang, YY
    Chen, H
    Li, XJ
    ACTA CHIMICA SINICA, 2005, 63 (20) : 1927 - 1930
  • [50] Synthesis of chiral 1,2-diamine immobilized on polystyrene and its application to asymmetric hydrogenation of aromatic ketones
    Takahashi, M
    Tsuji, A
    Chiba, M
    Itsuno, S
    REACTIVE & FUNCTIONAL POLYMERS, 2005, 65 (1-2): : 1 - 8
12345