Stereoselective syntheses of substituted tert-butyl 3-allyl-4-hydroxypiperidine-1-carboxylate

被引：0
|
作者：
V. I. Boev
A. I. Moskalenko
S. L. Belopukhov
N. M. Przheval’skii
机构：
[1] “Timiryazev Moscow Agricultural Academy” Russian State Agrarian University,
来源：
Russian Journal of Organic Chemistry | 2015年 / 51卷
关键词：
Oily Substance; Stereoselective Synthesis; Mitsunobu Reaction; Anhydrous Tetrahydrofuran; DIAD;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
tert-Butyl 3-allyl-4-oxopiperidine-1-carboxylate and its derivatives substituted at the 3-position and in the allylic fragment reacted with L-selectride in anhydrous tetrahydrofuran to give tert-butyl (3R,4S)-3-allyl-4-hydroxypiperidine-1-carboxylates (cis isomers) in quantitative yield. The Mitsunobu reaction of the latter with formic or benzoic acid, followed by alkaline hydrolysis, afforded the corresponding trans (3R,4R) isomers.
引用
收藏
页码：493 / 497
页数：4
相关论文
共 50 条
  • [1] Stereoselective syntheses of substituted tert-butyl 3-allyl-4-hydroxypiperidine-1-carboxylate
    Boev, V. I.
    Moskalenko, A. I.
    Belopukhov, S. L.
    Przheval'skii, N. M.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 51 (04) : 493 - 497
  • [2] tert-Butyl 1-hydroxypiperidine-2-carboxylate
    Bruecher, Oliver
    Bergstraesser, Uwe
    Kelm, Harald
    Hartung, Jens
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2061 - U741
  • [3] 3-allylation of tert-butyl 4-oxopiperidine-1-carboxylate
    Moskalenko, A. I.
    Boev, V. I.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 50 (11) : 1584 - 1589
  • [4] 3-allylation of tert-butyl 4-oxopiperidine-1-carboxylate
    A. I. Moskalenko
    V. I. Boev
    Russian Journal of Organic Chemistry, 2014, 50 : 1584 - 1589
  • [5] tert-Butyl 4-carbamoyl-3-methoxyimino-4-methylpiperidine-1-carboxylate
    Wang, Juxian
    Liu, Mingliang
    Cao, Jue
    Wang, Yucheng
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O2294 - U1911
  • [6] tert-Butyl 3-carbamoyl-4-methoxyimino-3-methylpiperidine-1-carboxylate
    Chai, Yun
    Wan, Zhi-Long
    Guo, Hui-Yuan
    Liu, Ming-Liang
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O282 - U1811
  • [7] tert-Butyl imidazole-1-carboxylate
    Kerscher, Tobias
    Prommnitz, Tanja
    Kluefers, Peter
    Mayer, Peter
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O405 - U2897
  • [8] tert-butyl 3-(4-bromophenylsulfonyl)pyrrolidine-1-carboxylate
    Yao, Zheng
    Li, Zhi-Gang
    Deng, Jian-Cheng
    Xu, Jing-Wei
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O3485 - U3253
  • [9] Synthesis of tert-butyl 4-bromo-4-formylpiperidine-1-carboxylate
    Hu, Xiaohan
    Zhao, Bingbing
    Zou, WenSheng
    Yang, Xuehui
    Zheng, Pengwu
    2018 4TH INTERNATIONAL CONFERENCE ON ENVIRONMENTAL SCIENCE AND MATERIAL APPLICATION, 2019, 252
  • [10] tert-Butyl 4-formyl-1H-imidazole-1-carboxylate
    Kang, Jun-Tao
    Li, Zhi-Gang
    Xu, Jing-Wei
    Wei, Yang
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O2185 - U2644
12345