A chiral ketone for enantioselective recognition of 1,2-amino alcohols

被引:15
|
作者
Nandhakumar, Raju
Guo, Yong-En
Park, Hytinjung
Tang, Lijun
Nam, Wonwoo
Kim, Kwan Mook [1 ]
机构
[1] Ewha Womans Univ, Dept Chem, Seoul 120750, South Korea
[2] Ewha Womans Univ, Div Nanosci, Seoul 120750, South Korea
基金
新加坡国家研究基金会;
关键词
chiral ketone; Enantioselective recognition; 1,2-Amino alcohols; imine bond;
D O I
10.1016/j.tetlet.2007.07.037
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel auxillary chiral ketone has been designed, synthesized, and used to enantioselectively recognize 1,2-amino alcohols. This work proves that the keto group can serve as a chiral recognition center by imine formation supported by resonance assisted hydrogen bonding (RAHB). (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6582 / 6585
页数:4
相关论文
共 50 条
  • [1] A Novel Dimeric BINOL for Enantioselective Recognition of 1,2-Amino Alcohols
    Velmurugan, Krishnaswamy
    Tang, Lijun
    Nandhakumar, Raju
    CHINESE JOURNAL OF CHEMISTRY, 2014, 32 (11) : 1157 - 1160
  • [2] Enantioselective Synthesis of Chiral 1,2-Amino Alcohols via Asymmetric Hydrogenation of α-Amino Ketones with Chiral Spiro Iridium Catalysts
    Yuan, Ming-Lei
    Xie, Jian-Hua
    Yang, Xiao-Hui
    Zhou, Qi-Lin
    SYNTHESIS-STUTTGART, 2014, 46 (21): : 2910 - 2916
  • [3] Asymmetric self-replication of chiral 1,2-amino alcohols by highly enantioselective autoinductive reduction
    Shibata, T
    Takahashi, T
    Konishi, T
    Soai, K
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (22): : 2458 - 2460
  • [4] Enantioselective recognition of 1,2-amino alcohols by reversible formation of imines with resonance-assisted hydrogen bonds
    Kim, KM
    Park, H
    Kim, HJ
    Chin, J
    Nam, W
    ORGANIC LETTERS, 2005, 7 (16) : 3525 - 3527
  • [5] Useful Applications of Enantioselective (4+2)-Cycloaddition Reactions to the Synthesis of Chiral 1,2-Amino Alcohols, 1,2-Diamines, and β-Amino Acids
    Reddy, Karla Mahender
    Thirupathi, Barla
    Corey, E. J.
    ORGANIC LETTERS, 2017, 19 (18) : 4956 - 4959
  • [6] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis
    Ager, DJ
    Prakash, I
    Schaad, DR
    CHEMICAL REVIEWS, 1996, 96 (02) : 835 - 875
  • [7] Chemistry for chiral skeletons: Building chiral fragments from enantiopure 1,2-amino alcohols
    Serrano, Juan
    Boskovic, Zarko
    Ferrara, Steven
    Furst, Laura
    Figueroa, Samuel
    Crews, DeMarcus
    Guerrero, Adrian
    Brackeen, Christina
    Nelson, Shawn
    Dandapani, Sivaraman
    Phillips, Andrew
    Schreiber, Stuart
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
  • [8] Chiral oxazolidinones from α-hydroxy oxazolidines:: a new access to 1,2-amino alcohols
    Agami, C
    Amiot, F
    Couty, F
    Dechoux, L
    Kaminsky, C
    Venier, O
    TETRAHEDRON-ASYMMETRY, 1998, 9 (22) : 3955 - 3958
  • [9] Asymmetric synthesis of 1,2-amino alcohols using (S)-indoline chiral auxiliary
    Youn, SW
    Choi, JY
    Kim, YH
    CHIRALITY, 2000, 12 (5-6) : 404 - 407
  • [10] Syntheses of 1,2-amino alcohols and their applications for oxazaborolidine catalyzed enantioselective reduction of aromatic ketones
    Vatmurge, Namdev S.
    Hazra, Braja G.
    Pore, Vandana S.
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2007, 60 (03) : 196 - 204