Concise Enantioselective Synthesis of Naturally Active (S)-3-Hydroxypiperidine

被引：6
|
作者：
Dey, Soumen [1 ]
Karabal, Pratibha U. [1 ]
Sudalai, Arumugam [1 ]
机构：
[1] CSIR Natl Chem Lab, Chem Engn & Proc Dev Div, Pune 411008, Maharashtra, India
来源：
SYNTHETIC COMMUNICATIONS | 2015年 / 45卷 / 13期
关键词：
Asymmetric synthesis; bioactivity; enantioselectivity; natural products; organocatalysis; ASYMMETRIC ALPHA-AMINOOXYLATION; KINETIC RESOLUTION; TERMINAL EPOXIDES; AMINOXYLATION; ALCOHOLS; OLEFINATION; AMINATION; ALDEHYDES; 1,2-DIOLS; FACILE;
D O I：
10.1080/00397911.2015.1033428
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A short and efficient enantioselective synthesis of natural product (S)-3-hydroxypiperidine has been achieved starting from commercially available raw materials employing two catalytic routes: (i) cocatalyzed hydrolytic kinetic resolution (HKR) of racemic methyl-3-(oxiran-2-yl)propanoate; (ii) proline-catalyzed -aminooxylation followed by Horner-Wardsworth-Emmons olefination in high enantiomeric purity (97% ee) and high overall yield (38%).
引用
收藏
页码：1559 / 1565
页数：7
相关论文
共 50 条
  • [1] The 3-Hydroxypiperidine Skeleton: Key Element in Natural Product Synthesis
    Wijdeven, Marloes A.
    Willemsen, Jorgen
    Rutjes, Floris P. J. T.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (15) : 2831 - 2844
  • [2] Facile Syntheses of Enantiopure 3-Hydroxypiperidine Derivatives and 3-Hydroxypipecolic Acids
    Chiou, Wen-Hua
    Lin, Gau-Hong
    Liang, Chih-Wei
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (05) : 1748 - 1751
  • [3] A concise enantioselective synthesis of marine macrolide-stagonolide E via organocatalysis
    Dey, Soumen
    Sudalai, Arumugam
    TETRAHEDRON-ASYMMETRY, 2015, 26 (07) : 344 - 349
  • [4] Versatile and Enantioselective Total Synthesis of Naturally Active Gnetulin
    Shang, Changhui
    Kang, Yulong
    Yang, Qingyun
    Zhu, Qibin
    Yao, Chunsuo
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (16) : 3768 - 3776
  • [5] Enantioselective Construction of 3-Hydroxypiperidine Scaffolds by Sequential Action of Light and Rhodium upon N-Allylglyoxylamides
    Ishida, Naoki
    Necas, David
    Masuda, Yusuke
    Murakami, Masahiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (25) : 7418 - 7421
  • [6] A concise enantioselective synthesis of the guaiane sesquiterpene (-)- oxyphyllol
    Zahel, Martin
    Metz, Peter
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 2028 - 2032
  • [7] A Concise Enantioselective Synthesis of (+)-L-733,060 and (+)-T-2328 via Sequential Proline Catalysis
    Lalwani, Komal G.
    Sudalai, Arumugam
    SYNLETT, 2016, 27 (09) : 1339 - 1343
  • [8] A concise enantioselective synthesis of (+)-α-conhydrine
    Nagata, K
    Toriizuka, Y
    Itoh, T
    HETEROCYCLES, 2005, 66 : 107 - 109
  • [9] A concise enantioselective synthesis of (+)-febrifugine
    Emmanuvel, Lourdusamy
    Kamble, Dayanand A.
    Sudalai, Arumugam
    TETRAHEDRON-ASYMMETRY, 2009, 20 (01) : 84 - 88
  • [10] A concise enantioselective synthesis of (+)-lentiginosine
    Shaikh, Tanveer Mahamadali
    Sudalai, Arumugam
    TETRAHEDRON-ASYMMETRY, 2009, 20 (19) : 2287 - 2292
12345