Chemo-, regio- and stereoselective Mitsunobu reaction of unprotected pyrimidine bases with hydroxypyrrolidines

被引：13
|
作者：
Richichi, B
Cicchi, S
Chiacchio, U
Romeo, G
Brandi, A
机构：
[1] Univ Messina, Dipartimento Farmacochim, I-98100 Messina, Italy
[2] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy
[3] Univ Florence, Dipartimento Chim Organ Ugo Schiff, I-50019 Florence, Italy
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 22期
关键词：
Mitsunobu reaction; pyrrolidine; pyrimidine bases;
D O I：
10.1016/S0040-4039(02)00712-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Unprotected pyrimidine bases were used in Mitsunobu reaction to afford in high yield new substituted pyrrolidines. The reaction is chemo-, regio- and stereoselective affording exclusively N-1 alkylated derivatives of (3S)-N-benzyl-3-hydroxy-pyrrolidine and (3S,4S)-N-benzyl-3,4-dihydroxypyrrolidine. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：4013 / 4015
页数：3
相关论文
共 5 条
  • [1] Mitsunobu Reaction of 1,2,3-NH-Triazoles: A Regio- and Stereoselective Approach to Functionalized Triazole Derivatives
    Yan, Wuming
    Liao, Tao
    Tuguldur, Odbadrakh
    Zhong, Cheng
    Petersen, Jeffrey L.
    Shi, Xiaodong
    CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) : 2720 - 2724
  • [2] A highly atom economic, chemo-, regio- and stereoselective synthesis, and discovery of spiro-pyrido-pyrrolizines and pyrrolidines as antimycobacterial agents
    Kumar, Raju Ranjith
    Perumal, Subbu
    Senthilkumar, Palaniappan
    Yogeeswari, Perumal
    Sriram, Dharmarajan
    TETRAHEDRON, 2008, 64 (13) : 2962 - 2971
  • [3] Intramolecular Mitsunobu reaction in the regio- and stereoselective synthesis of cis-4,5-disubstituted piperidin-2-ones
    Langlois, N
    Calvez, O
    TETRAHEDRON LETTERS, 2000, 41 (43) : 8285 - 8288
  • [4] 1, 2-trans-Stereoselective 7-O-Glycosylation of Flavonoids with Unprotected Pyranoses by Mitsunobu Reaction
    Shi, Hailong
    Yang, Jian
    Cheng, Yao
    Yang, Jinlian
    Lu, Xiaoxia
    Ma, Xiaofeng
    CHEMISTRY-AN ASIAN JOURNAL, 2022, 17 (09)
  • [5] Regio- and stereoselective synthesis of new spirooxindoles via 1,3-dipolar cycloaddition reaction: Anticancer and molecular docking studies
    Lofty, Gehad
    El Ashry, El Sayed H.
    Said, Mohamed M.
    El Tamany, El Sayed
    Aziza, Yasmine M. Abdel
    Al-Dhfyan, Abdullah
    Al-Majid, Abdullah M.
    Barakat, Assem
    JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 2018, 180 : 98 - 108
1