Regioselective Ring-Opening of Amino Acid-Derived Chiral Aziridines: an Easy Access to cis-2,5-Disubstituted Chiral Piperazines

被引：27
|
作者：
Samanta, Krishnananda [1 ]
Panda, Gautam [1 ]
机构：
[1] Cent Drug Res Inst, Div Med & Proc Chem, Lucknow 226001, Uttar Pradesh, India
来源：
CHEMISTRY-AN ASIAN JOURNAL | 2011年 / 6卷 / 01期
关键词：
amino acids; cyclization; heterocycles; natural products; regioselectivity; MITSUNOBU; POTENT; INHIBITORS; CHEMISTRY;
D O I：
10.1002/asia.201000554
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient four-step synthetic strategy for cis-2,5-disubstituted chiral piperazines derived from amino-acid-based aziridines is described. The key steps in this strategy are the highly regioselective boron trifluoride diethyl etherate (BF3 center dot OEt2)-mediated ring-opening of less-reactive N-Ts chiral aziridines by alpha-amino acid methyl ester hydrochloride followed by Mitsunobu cyclization. This protocol has been used in an attempt to construct the piperazine core framework of natural product (+)-piperazinomycin.
引用
收藏
页码：189 / 197
页数：9
相关论文
共 36 条
  • [11] Ring-opening of N-alkoxycarbonyl γ-lactams with lithium methylphenylsulphone:: application to the synthesis of cis 2,5-disubstituted pyrrolidines
    Mota, AJ
    Langlois, N
    TETRAHEDRON LETTERS, 2003, 44 (06) : 1141 - 1143
  • [12] Synthesis and anionic ring-opening polymerization behavior of amino acid-derived cyclic carbonates
    Sanda, F
    Kamatani, J
    Endo, T
    MACROMOLECULES, 2001, 34 (06) : 1564 - 1569
  • [13] Regio- and diastereoselective ring-opening of (S)-(-)-2-(trifluoromethyl)oxirane with chiral 2,5-disubstituted tetrahydroquinolines in hexafluoro-2-propanol
    Li, Xun
    Russell, Ronald K.
    Chen, Hongfeng
    Zhang, Yongzheng
    Ballentine, Scott
    Spink, Jan
    Branum, Shawn
    Liu, Fuqiang
    Chen, Yanping
    Rammeloo, Thomas
    Aelterman, Wim
    Sorgi, Kirk L.
    Murray, William V.
    GREEN CHEMISTRY, 2010, 12 (09) : 1548 - 1551
  • [14] Preparation of alpha,beta-diamino acid derivatives using regioselective ring opening of chiral aziridines.
    Shin, SH
    Lee, WK
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U182 - U182
  • [15] Gold-Catalyzed Regioselective Hydration of Homopropargyl Alcohols Followed by Diastereoselective Reduction: An Easy Access to cis 2,5-Disubstituted Tetrahydrofurans
    Thi Xuan Mai Nguyen
    Seon-Meniel, Blandine
    Jullian, Jean-Christophe
    Figadere, Bruno
    LETTERS IN ORGANIC CHEMISTRY, 2009, 6 (08) : 630 - 636
  • [16] Parallel kinetic resolution of aziridines via chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening
    Liu, Juan
    Du, Yi-Ying
    He, Yu-Shi
    Liang, Yan
    Liu, Shang-Zhong
    Li, Yi-Yi
    Cao, Yi-Ming
    CHEMICAL SCIENCE, 2023, 14 (43) : 12152 - 12159
  • [17] Regioselective nucleophilic ring-opening reaction of chiral epoxyallyl alcohols: a ready access to the pyran core of macrolactin 3
    Krishna, Palakodety Radha
    Nomula, Rajesh
    Krishna, Kallaganti V. S. Rama
    TETRAHEDRON LETTERS, 2014, 55 (22) : 3381 - 3383
  • [18] I2-Mediated Diversity Oriented Diastereoselective Synthesis of Amino Acid Derived trans-2,5-Disubstituted Morpholines, Piperazines, and Thiomorpholines
    Bera, Saurav
    Panda, Gautam
    ACS COMBINATORIAL SCIENCE, 2012, 14 (01) : 1 - 4
  • [19] Asymmetric Substitution at the Tetrasubstituted Chiral Carbon: Catalytic Ring-Opening Alkylation of Racemic 2,2-Disubstituted Aziridines with 3-Substituted Oxindoles
    Ohmatsu, Kohsuke
    Ando, Yuichiro
    Ooi, Takashi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (50) : 18706 - 18709
  • [20] Highly efficient regio-selective ring-opening nucleophilic fluorination of aziridines and azetidines: access to β- or γ-fluorinated amino acid derivatives
    Zhu, Liping
    Xiong, Jiale
    An, Junkai
    Chen, Nannan
    Xue, Jijun
    Jiang, Xianxing
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (15) : 3797 - 3804
1234