Solvent Directed Diastereodivergent Synthesis of Spiro-Oxindoles with Quaternary Carbon Center Forming

被引：2
作者：
Zhang, Yang [1 ]
Liao, Qian [1 ]
Liu, Jin-Yu [1 ]
Yang, Ming-Wen [1 ]
机构：
[1] Chengdu Univ Technol, Coll Mat & Chem & Chem Engn, Chengdu 610059, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 26卷 / 38期
关键词：
catalysis; diastereodivergent synthesis; quaternary carbon center; solvent effects; spiro-oxindole; ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS; CRAFTS CASCADE REACTION; ALPHA; BETA-UNSATURATED ALDEHYDES; CYCLOADDITION REACTION; INDOLE ALKALOIDS; CONSTRUCTION; DERIVATIVES; CATALYSIS;
D O I：
10.1002/ejoc.202300787
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient method has been developed for the solvent-directed diastereodivergent cyclization reactions with quaternary center formation. Various spiro-oxindole diastereoisomers were synthesized with good yields (up to >99 %) and moderate to high diastereoselectivities (up to >20 : 1). Further study on NMR studies indicates that the key to this approach lies in different interactions between the substrate and organocatalyst across diverse solvents. This methodology may have significant implications for switchable, solvent-directed diastereodivergent synthesis.
引用
收藏
页数：7
相关论文
共 50 条
  • [41] Lipase-catalyzed kinetic resolution of α-hydroxymethylcycloalkanones with a quaternary carbon center. Chemoenzymatic synthesis of chiral pseudoiridolactones
    Guerrab, Zineb
    Schweiger, Stefan
    Daou, Boujemaa
    Ahmar, Mohammed
    Cazes, Bernard
    TETRAHEDRON-ASYMMETRY, 2010, 21 (13-14) : 1752 - 1757
  • [42] Catalytic Enantioselective Synthesis of 3,4-Polyfused Oxindoles with Quaternary All-Carbon Stereocenters: A Rh-Catalyzed C-C Activation Approach
    Qiu, Bo
    Li, Xiao-Tong
    Zhang, Jian-Yu
    Zhan, Jun-Ling
    Huang, Shuang-Ping
    Xu, Tao
    ORGANIC LETTERS, 2018, 20 (23) : 7689 - 7693
  • [43] Enantioselective Synthesis of Nitriles Containing a Quaternary Carbon Center by Michael Reactions of Silyl Ketene Imines with 1-Acrylpyrazoles
    Chen, Long
    Pu, Maoping
    Li, Shiyang
    Sang, Xinpeng
    Liu, Xiaohua
    Wu, Yun-Dong
    Feng, Xiaoming
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (45) : 19091 - 19098
  • [44] Stereoselective Synthesis of (Z)-Dihomoallylic Phosphonates with Quaternary Carbon Center by Palladium-Catalyzed Bisallylation of Vinylethyene Carbonates with β-Ketophosphonates
    Liu, Zhigang
    Ke, Miaolin
    Zhang, Ke
    Zuo, Sheng
    Jiang, Meifen
    Chen, Fener
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (04) : 757 - 761
  • [45] Enantioselective desymmetrizing palladium catalyzed carbonylation reactions: the catalytic asymmetric synthesis of quaternary carbon center containing 1,3-dienes
    Byrne, Simon J.
    Fletcher, Anthony J.
    Hebeisen, Paul
    Willis, Michael C.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (04) : 758 - 760
  • [46] Synthesis of Fluorenes with an All-Carbon Quaternary Center via Palladium-Catalyzed Dual Arylation using Cyclic Diaryliodonium Triflates
    Peng, Xiaopeng
    Luo, Hongwen
    Wu, Fuhai
    Zhu, Daqian
    Ganesan, A.
    Huang, Peng
    Wen, Shijun
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (07) : 1152 - 1156
  • [47] Chemo-selective Rh(II)/Pd(0) Dual Catalysis: Synthesis of All-Carbon C3-Quaternary Allylic Oxindoles from N-Aryl-α-Diazo-β-Keto-Amides with Functionalized Allyl Carbonates
    Chen, Ling-Hang
    Ma, Yang-Ting
    Yang, Fang
    Huang, Xiao-Yan
    Chen, Shu-Wei
    Ji, Kegong
    Chen, Zi-Sheng
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (06) : 1307 - 1312
  • [48] Primary Amine, Thiourea-Based Dual Catalysis Motif for Synthesis of Stereogenic, All-Carbon Quaternary Center-Containing Cycloalkanones
    Kang, Jun Yong
    Carter, Rich G.
    ORGANIC LETTERS, 2012, 14 (12) : 3178 - 3181
  • [49] Chiral Calcium Phosphate Catalyzed Enantioselective Synthesis of All-Carbon Quaternary Center by Friedel-Crafts Alkylation Reaction of Pyrroles and Trifluoromethylated Nitrostyrenes
    Uchikura, Tatsuhiro
    Yokohama, Sosuke
    Murakami, Mona
    Akiyama, Takahiko
    SYNTHESIS-STUTTGART, 2022, 54 (17): : 3793 - 3800
  • [50] Dimethyl Sulfoxide Provides Three Different Units in Synthesis of Chroman-4-ones Containing Sulfur and a Quaternary Carbon Center under HOAc Conditions
    Xu, Lihong
    Wang, Anan
    Shi, Xu
    He, Qian
    Jiang, Tao-Shan
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (19) : 13466 - 13474
12345