Phosphine-catalyzed enantioselective [3+2] annulations of 2,3-butadienoates with imines

被引：120
|
作者：
Jean, L [1 ]
Marinetti, A [1 ]
机构：
[1] CNRS, Inst Chim Subst Nat, UPR 2301, F-91198 Gif Sur Yvette, France
来源：
TETRAHEDRON LETTERS | 2006年 / 47卷 / 13期
关键词：
3+2] cycloadditions; enantioselective organocatalysis; phosphines; 3-pyrrolines;
D O I：
10.1016/j.tetlet.2006.01.122
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first systematic screening of chiral phosphines in the cycloaddition reaction between 2,3-butadienoates and arylimines has led to the identification of fairly efficient catalysts. 2-Aryl-3-pyrrolines have been obtained with enantiomeric excesses up to 64%. In one instance, the enantiomeric excess could be increased to 91% ee by combining the enantioselective cyclization reaction with a crystallization step. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2141 / 2145
页数：5
相关论文
共 50 条
  • [21] Enantioselective total synthesis of (+)-ibophyllidine via an asymmetric phosphine-catalyzed [3+2] annulation
    Andrews, Ian P.
    Kwon, Ohyun
    CHEMICAL SCIENCE, 2012, 3 (08) : 2510 - 2514
  • [22] Phosphine-catalyzed activation of cyclopropenones: a versatile C3 synthon for (3+2) annulations with unsaturated electrophiles
    He, Xin
    Ma, Pengchen
    Tang, Yuhai
    Li, Jing
    Shen, Shenyu
    Lear, Martin J.
    Houk, K. N.
    Xu, Silong
    CHEMICAL SCIENCE, 2022, 13 (43) : 12769 - 12775
  • [23] Unraveling the Selectivity Patterns in Phosphine-Catalyzed Annulations of Azomethine Imines and Allenoates
    Gallardo-Fuentes, Sebastian
    Ormazabal-Toledo, Rodrigo
    Fernandez, Israel
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (14): : 9272 - 9280
  • [24] Phosphine-catalyzed asymmetric [3+2] annulation of chalcones with allenoates for enantioselective synthesis of functionalized cyclopentenes
    Gao, Zhenzhen
    Wang, Chang
    Yuan, Chunhao
    Zhou, Leijie
    Sun, Zhanhu
    Xiao, Yumei
    Guo, Hongchao
    RSC ADVANCES, 2015, 5 (127): : 105359 - 105362
  • [25] Phosphine-Catalyzed Dearomative [3+2] Cycloaddition of Benzoxazoles with a Cyclopropenone
    Wang, Xingben
    Yu, Congjun
    Atodiresei, Iuliana L.
    Patureau, Frederic W.
    ORGANIC LETTERS, 2022, 24 (05) : 1127 - 1131
  • [26] Phosphine-Catalyzed [3+2] Cyclizations: Applications to the Enantioselective Synthesis of Cyclopentene-Fused Chromanones and Dihydroquinolinones
    Neel, Mathilde
    Gouin, Jerome
    Voituriez, Arnaud
    Marinetti, Angela
    SYNTHESIS-STUTTGART, 2011, (12): : 2003 - 2009
  • [27] Enantioselective One-Pot Synthesis of α-Amino Esters by a Phosphine-Catalyzed [3+2]-Cycloaddition Reaction
    Steurer, Marianne
    Jensen, Kim L.
    Worgull, Dennis
    Jorgensen, Karl Anker
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (01) : 76 - 79
  • [28] Phosphine-Catalyzed [3+2] Annulation of β-Sulfonannido-Substituted Enones with Sulfamate-Derived Cyclic Imines
    Shi, Wangyu
    Zhou, Leijie
    Mao, Biming
    Wang, Qijun
    Wang, Chang
    Zhang, Cheng
    Li, Xuefeng
    Xiao, Yumei
    Guo, Hongchao
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (02): : 679 - 686
  • [29] Phosphine-catalyzed [3+2] annulation of α-substituted allenoates with ester-activated α,β-unsaturated imines: a novel variation of the Lu [3+2] cycloaddition reaction
    Tian, Junjun
    He, Zhengjie
    CHEMICAL COMMUNICATIONS, 2013, 49 (20) : 2058 - 2060
  • [30] Phosphine-Catalyzed (3+2)/(3+2) Sequential Annulation of γ-Vinyl Allenoates: Access to Fused Carbocycles
    Feng, Jiaxu
    Chen, Yingying
    Qin, Wenhui
    Huang, You
    ORGANIC LETTERS, 2020, 22 (02) : 433 - 437
12345