Dynamic kinetic resolution of α-chloro esters in asymmetric nucleophilic substitution using diacetone-D-glucose as a chiral auxiliary

被引：25
|
作者：
Kim, HJ [1 ]
Shin, EK [1 ]
Chang, JY [1 ]
Kim, Y [1 ]
Park, YS [1 ]
机构：
[1] Konkuk Univ, Dept Chem, Seoul 143701, South Korea
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 23期
关键词：
dynamic kinetic resolution; asymmetric syntheses; nucleophilic substitution; carbohydrate; chiral auxiliary;
D O I：
10.1016/j.tetlet.2005.04.003
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Diacetone-D-glucose mediated dynamic kinetic resolution of alpha-chloro-alpha-aryl esters in nucleophilic substitution reactions has been investigated. Reactions of various amine nucleophiles in the presence of TBAI and DIEA can provide the substitution products 2-10 up to 97% yield and 97:3 dr. This simple procedure with easy removal of the chiral auxiliary provides a practical protocol for asymmetric syntheses of alpha-amino acid derivatives up to 97:3 er. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4115 / 4117
页数：3
相关论文
共 10 条
  • [1] Asymmetric syntheses of N-substituted α-amino esters via dynamic kinetic resolution of α-haloacyl diacetone-D-glucose
    Jung Kim, Hyun
    Kim, Yongtae
    Ta Choi, Eui
    Hee Lee, Min
    Sun No, Eun
    Sun Park, Yong
    TETRAHEDRON, 2006, 62 (26) : 6303 - 6311
  • [2] Dynamic kinetic resolution of α-bromo carboxylic acid derivatives in asymmetric nucleophilic substitution with chiral α-amino esters
    Chang, JY
    Shin, EK
    Kim, HJ
    Kim, Y
    Park, YS
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2005, 26 (06): : 989 - 992
  • [3] Diisopropyl L-Malate as a New Chiral Auxiliary for Dynamic Kinetic Resolution of α-Bromo Esters and Asymmetric Syntheses of Aminoflavones and Dihydroquinoxalinones
    Kang, Kyoung Hee
    Jang, Jung In
    Bin Baek, Seung
    Ahn, Jung Hee
    Park, Yong Sun
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (05) : 1741 - 1744
  • [4] Asymmetric nucleophilic substitution of α-bromo amides via dynamic kinetic resolution for the preparation of dipeptide analogues
    Nam, J
    Chang, JY
    Shin, EK
    Kim, HJ
    Kim, Y
    Jang, S
    Park, YS
    TETRAHEDRON, 2004, 60 (30) : 6311 - 6318
  • [5] Dynamic kinetic resolution of (S)-mandelate-derived α-bromo esters in nucleophilic substitution and asymmetric syntheses of 3-substituted morpholin-2-ones
    Lee, Yoon Min
    Kang, Kyoung Hee
    Min, Hye-Min
    Lim, Hyun Jin
    Park, Eun-Hyung
    Park, Yong Sun
    ARKIVOC, 2010, : 1 - 15
  • [6] A NEW ENANTIOSELECTIVE SYNTHESIS OF GLYCIDATES VIA DYNAMIC KINETIC RESOLUTION OF RACEMIC 2-CHLORO-3-KETO ESTERS USING CHIRAL RU(II) COMPLEXES
    GENET, JP
    DEANDRADE, MCC
    RATOVELOMANANAVIDAL, V
    TETRAHEDRON LETTERS, 1995, 36 (12) : 2063 - 2066
  • [7] Dynamic Kinetic Resolution Approach for the Asymmetric Synthesis of Tetrahydrobenzodiazepines Using Transfer Hydrogenation by Chiral Phosphoric Acid
    Horiguchi, Kosaku
    Yamamoto, Eri
    Saito, Kodai
    Yamanaka, Masahiro
    Akiyama, Takahiko
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (24) : 8078 - 8083
  • [8] Dynamic kinetic resolution of β′-keto-β-amino esters using Ru-DTBM-Sunphos catalyzed asymmetric hydrogenation
    Li, Xiaoming
    Tao, Xiaoming
    Ma, Xin
    Li, Wanfang
    Zhao, Mengmeng
    Xie, Xiaomin
    Ayad, Tahar
    Ratovelomanana-Vidal, Virginie
    Zhang, Zhaoguo
    TETRAHEDRON, 2013, 69 (34) : 7152 - 7156
  • [9] First Asymmetric Total Synthesis of Salinosporamides D and I Using Memory of Chirality and Dynamic Kinetic Resolution
    Park, Soojun
    Jeong, Yeji
    Lim, Changhyun
    Kim, Sanghee
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (39)
  • [10] Dynamic Kinetic Resolution for Asymmetric Synthesis of L-Noncanonical Amino Acids from D-Ser Using Tryptophan Synthase and Alanine Racemase
    Yu, Jinhai
    Li, Jing
    Gao, Xia
    Zeng, Shuiyun
    Zhang, Hongjuan
    Liu, Junzhong
    Jiao, Qingcai
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (39) : 6618 - 6625
1