Organocatalytic regio- and enantioselective vinylogous aza-Morita-Baylis-Hillman reaction

被引：2
|
作者：
Gondo, Naruhiro [1 ]
Fujimura, Koki [1 ]
Hyakutake, Ryuichi [1 ]
Ueda, Yoshihiro [1 ]
Kawabata, Takeo [1 ,2 ]
机构：
[1] Kyoto Univ, Inst Chem Res, Uji, Kyoto 6110011, Japan
[2] Int Univ Hlth & Welf, Dept Pharmaceut Sci, 137-1 Enokizu, Okawa, Fukuoka 831501, Japan
来源：
TETRAHEDRON LETTERS | 2023年 / 115卷
关键词：
Asymmetric organocatalysis; Aza-Morita-Baylis-Hillman reaction; Chiral amine; Regioselectivity; 7-Selectivity; SITE-SELECTIVE ACYLATION; CATALYSTS; ACID; FUNCTIONALIZATION; ELLAGITANNINS; ACTIVATION; MECHANISM; STRATEGY; IMINES;
D O I：
10.1016/j.tetlet.2022.154306
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Asymmetric regioselective vinylogous aza-Morita-Baylis-Hillman reactions by organocatalysis were developed. The reactions of 3-vinylcyclopentenone with various aldimines in the presence of chiral pyrrolidinopyridine catalysts gave the 7-adducts in high regioselectivity and moderate enantioselectivity.(c) 2022 Elsevier Ltd. All rights reserved.
引用
收藏
页数：5
相关论文
共 50 条
  • [31] Chiral thiourea-phosphine organocatalysts in the asymmetric Aza-Morita-Baylis-Hillman reaction
    Shi, Yong-Ling
    Shi, Min
    ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (13) : 2129 - 2135
  • [32] Enantioselective Trifunctional Organocatalysts for Rate-Enhanced Aza-Morita-Baylis-Hillman Reactions at Room Temperature
    Garnier, Jean-Marc
    Anstiss, Christopher
    Liu, Fei
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (03) : 331 - 338
  • [33] Enantioselective Acid-Base Organocatalyzed Domino Reactions Based on aza-Morita-Baylis-Hillman Process
    Takizawa, Shinobu
    Sasai, Hiroaki
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2014, 72 (07) : 781 - 796
  • [34] Aza-Morita-Baylis-Hillman reaction with ion-supported Ph3P
    Imura, Yumi
    Shimojuh, Naoya
    Moriyama, Katsuhiko
    Togo, Hideo
    TETRAHEDRON, 2012, 68 (10) : 2319 - 2325
  • [35] Enantioselective Organocatalytic Intramolecular Morita-Baylis-Hillman Reaction of Some Unusual Substrates
    Satpathi, Bishnupada
    Ramasastry, S. S. V.
    SYNLETT, 2016, 27 (15) : 2178 - 2182
  • [36] P-chirogenic organocatalysts: application to the aza-Morita-Baylis-Hillman (aza-MBH) reaction of ketimines
    Takizawa, Shinobu
    Remond, Emmanuelle
    Arteaga, Fernando Arteaga
    Yoshida, Yasushi
    Sridharan, Vellaisamy
    Bayardon, Jerome
    Juge, Sylvain
    Sasai, Hiroaki
    CHEMICAL COMMUNICATIONS, 2013, 49 (75) : 8392 - 8394
  • [37] Asymmetric organocatalytic Morita-Baylis-Hillman reaction and asymmetric organocatalytic transformations of Morita-Baylis-Hillman adducts. An update
    Pellissier, Helene
    TETRAHEDRON, 2025, 172
  • [38] Asymmetric catalytic aza-Morita-Baylis-Hillman reaction using chiral bifunctional phosphine amides as catalysts
    Qi, Ming-Juan
    Ai, Teng
    Shi, Min
    Li, Guigen
    TETRAHEDRON, 2008, 64 (07) : 1181 - 1186
  • [39] Conformational lock in a Bronsted acid-Lewis base organocatalyst for the aza-Morita-Baylis-Hillman reaction
    Matsui, K
    Tanaka, K
    Horii, A
    Takizawa, S
    Sasai, H
    TETRAHEDRON-ASYMMETRY, 2006, 17 (04) : 578 - 583
  • [40] Chiral phosphine-catalyzed regio- and enantioselective allylic amination of Morita-Baylis-Hillman acetates
    Ma, Guang-Ning
    Cao, Shu-Hua
    Shi, Min
    TETRAHEDRON-ASYMMETRY, 2009, 20 (09) : 1086 - 1092
12345