Diastereoselective Synthesis of Multisubstituted Chroman Derivatives via Iminium Formation/Morita-Baylis-Hillman Reaction/Oxa-Michael Reaction Sequence

被引：1
|
作者：
Ido, Natsuki [1 ]
Mori, Keiji [1 ]
机构：
[1] Tokyo Univ Agr & Technol, Dept Appl Chem, Grad Sch Engn, 2-24-16 Nakacho, Koganei, Tokyo 1848588, Japan
来源：
CHEMISTRY LETTERS | 2019年 / 48卷 / 04期
关键词：
One-pot reaction; Chroman; Diastereoselective reactions; C(SP(3))-H BOND FUNCTIONALIZATION; CIS-FUSED PYRANO; ANTIHYPERTENSIVE ACTIVITY; EXPEDITIOUS SYNTHESIS; ASYMMETRIC-SYNTHESIS; PYRANOBENZOPYRANS; FURANOBENZOPYRANS; CONSTRUCTION; ACTIVATION; SKELETON;
D O I：
10.1246/cl.180988
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A one-pot, highly diastereoselective synthesis of chroman derivatives with three contiguous stereogenic centers is described. In this reaction, three transformations (iminium formation/Morita-Baylis-Hillman reaction/oxa-Michael reaction) occurred successively to afford multisubstituted chroman derivatives in moderate chemical yields with excellent diastereoselectivities (d.r. = >20:1:1:1).
引用
收藏
页码：337 / 340
页数：4
相关论文
共 50 条
  • [1] Oxa-Michael Addition Reaction and Polymerization of Morita-Baylis-Hillman Adducts and Derivatives
    Matsuoka, Shin-ichi
    Hoshiyama, Yuki
    Tsuchimoto, Kanae
    Suzuki, Masato
    CHEMISTRY LETTERS, 2017, 46 (12) : 1718 - 1720
  • [2] Heck Reaction on Morita-Baylis-Hillman Adducts: Diastereoselective Synthesis of Pyrrolizidinones and Pyrrolizidines
    de Luna Freire, Kristerson R.
    Tormena, Claudio F.
    Coelho, Fernando
    SYNLETT, 2011, (14) : 2059 - 2063
  • [3] Morita-Baylis-Hillman reaction of acrylamide with isatin derivatives
    Singh, Radhey M.
    Bharadwaj, Kishor Chandra
    Tiwari, Dharmendra Kumar
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 : 2975 - 2980
  • [4] Synthesis of sultam scaffolds via intramolecular oxa-Michael and diastereoselective Baylis-Hillman reactions
    Zhou, Aihua
    Hanson, Paul R.
    ORGANIC LETTERS, 2008, 10 (14) : 2951 - 2954
  • [5] An unexpected organocatalytic asymmetric tandem Michael/Morita-Baylis-Hillman reaction
    Cabrera, Silvia
    Aleman, Jose
    Bolze, Patrick
    Bertelsen, Soren
    Jorgensen, Karl Anker
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (01) : 121 - 125
  • [6] Synthesis of Multisubstituted Indanedione Based Spiropyrans via Oxa-Michael/Michael Cascade Reaction
    Reddy, Yeruva Pavankumar
    Gudise, Veera Babu
    Settipalli, Poorna Chandrasekhar
    Anwar, Shaik
    CHEMISTRYSELECT, 2021, 6 (18): : 4456 - 4460
  • [7] Synthesis of partially fluorinated β-amino acids via Morita-Baylis-Hillman reaction
    Sergeeva, NN
    Golubev, AS
    Burger, K
    SYNTHESIS-STUTTGART, 2001, (02): : 281 - 285
  • [8] Applications of the Morita-Baylis-Hillman Reaction in the Synthesis of Heterocyclic Systems
    Kaye, Perry T.
    ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 127, 2019, 127 : 101 - 152
  • [9] Work toward the total synthesis of pycnanthuquinone A via an asymmetric Morita-Baylis-Hillman reaction
    Wensley, Allison M.
    Schaus, Scott E.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [10] Enantioselective Michael Reaction of Cyclic β-Ketoesters with Morita-Baylis-Hillman Derivatives Using a Phase-Transfer Catalyst
    Takagi, Ryukichi
    Fujii, Emi
    Kondo, Hirotoshi
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (18): : 11191 - 11203
12345