Synthesis of chiral 3-substituted isoxazolidines.

被引:4
|
作者
Farr, RN [1 ]
机构
[1] Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA
关键词
D O I
10.1016/S0040-4039(97)10523-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of chiral (>98% ee) 3-substituted isoxazolidines has been achieved. Glycidyl tosylate was utilized to establish the desired stereochemistry in a "double grignard" reaction sequence. Mesylate displacement followed by acid-catalyzed cyclization allows the parent isoxazolidines to be obtained. (C) 1997 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:195 / 196
页数:2
相关论文
共 50 条
  • [21] Stereoselective synthesis of 3-substituted tetrahydroisoquinolines from phthalan and chiral N-sulfinylimines
    Garcia, Daniel
    Moreno, Benjamin
    Soler, Tatiana
    Foubelo, Francisco
    Yus, Miguel
    TETRAHEDRON LETTERS, 2009, 50 (33) : 4710 - 4713
  • [22] Synthesis and Application of 3-Substituted (S)-BINOL as Chiral Ligands for the Asymmetric Ethylation of Aldehydes
    Zhang, Zhi-Guang
    Dong, Zhi-Bing
    Li, Jin-Shan
    CHIRALITY, 2010, 22 (09) : 820 - 826
  • [23] Synthesis of chiral 3-substituted indanones via an enantioselective reductive-heck reaction
    Minatti, Ana
    Zheng, Xiaolai
    Buchwald, Stephen L.
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (24): : 9253 - 9258
  • [24] Efficient synthesis of 3-substituted coumarins
    Mashraqui, SH
    Vashi, D
    Mistry, HD
    SYNTHETIC COMMUNICATIONS, 2004, 34 (17) : 3129 - 3134
  • [25] A facile synthesis and asymmetric catalytic activity of new 3-substituted chiral BINOL ligands
    Liu, Bing
    Fang, Cao
    Dong, Zhi-Bing
    Li, Jin-Shan
    APPLIED ORGANOMETALLIC CHEMISTRY, 2008, 22 (01) : 55 - 58
  • [26] Highly enantioselective synthesis of chiral 3-substituted indolines by catalytic asymmetric hydrogenation of indoles
    Kuwano, R
    Kaneda, K
    Ito, T
    Sato, K
    Kurokawa, T
    Ito, Y
    ORGANIC LETTERS, 2004, 6 (13) : 2213 - 2215
  • [27] Chiral oxaziridines in the enantioselective synthesis of isoxazolidines
    Troisi, Luigino
    De Lorenzis, Sara
    Fabio, Marilena
    Rosato, Francesca
    Granito, Catia
    TETRAHEDRON-ASYMMETRY, 2008, 19 (19) : 2246 - 2251
  • [28] ENANTIOSPECIFIC SYNTHESIS OF 3-SUBSTITUTED ALKYLIDINECYCLOPENTANES
    MARTINEZ, AG
    VILAR, ET
    BARCINA, JO
    ALONSO, JM
    HERRERO, ER
    HANACK, M
    SUBRAMANIAN, LR
    TETRAHEDRON LETTERS, 1992, 33 (05) : 607 - 608
  • [29] A VERSATILE SYNTHESIS OF 3-SUBSTITUTED INDAZOLES
    KIM, BC
    KIM, JI
    JAHNG, YD
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1994, 15 (02) : 97 - 98
  • [30] Facile synthesis of 3-substituted isoindolinones
    Al-Jaroudi, Zainab
    Mohapatra, Prabhu P.
    Jha, Amitabh
    TETRAHEDRON LETTERS, 2016, 57 (07) : 772 - 777