Titanium-Catalyzed Stereoselective Synthesis of Spirooxindole Oxazolines

被引：63
|
作者：
Badillo, Joseph J. [1 ]
Arevalo, Gary E. [1 ]
Fettinger, James C. [1 ]
Franz, Annaliese K. [1 ]
机构：
[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 03期
关键词：
FORMAL 3+2 CYCLOADDITIONS; LEWIS-ACID; SPIROCYCLIC OXINDOLES; DIETHYL OXOMALONATE; 5-ALKOXYOXAZOLES; DERIVATIVES; ALDEHYDES; POTENT; 2-OXAZOLINE-4-CARBOXYLATES; DISCOVERY;
D O I：
10.1021/ol1027305
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A regio- and stereoselective cyclization between isatins and 5-methoxyoxazoles has been developed using catalytic titanium(IV) chloride (10 or 20 mol %) to afford spiro[3,3'-oxindoleoxazolines] in excellent yield (up to 99%) and diastereoselectivity (dr >99:1). Substitution at the 4-position of the oxazole controls nucleophilic attack to provide either the 2-oxazoline or 3-oxazoline spirocycle with excellent (>99:1) regiocontrol.
引用
收藏
页码：418 / 421
页数：4
相关论文
共 50 条
  • [1] Titanium(IV)-Catalyzed Stereoselective Synthesis of Spirooxindole-1-pyrrolines
    Badillo, Joseph J.
    Ribeiro, Carlos J. A.
    Olmstead, Marilyn M.
    Franz, Annaliese K.
    [J]. ORGANIC LETTERS, 2014, 16 (24) : 6270 - 6273
  • [2] Titanium-catalyzed stereoselective geminal heterodihalogenation of β-ketoesters
    Frantz, R
    Hintermann, L
    Perseghini, M
    Broggini, D
    Togni, A
    [J]. ORGANIC LETTERS, 2003, 5 (10) : 1709 - 1712
  • [3] Stereoselective Synthesis of Tertiary Allylic Amines by Titanium-Catalyzed Hydroaminoalkylation of Alkynes with Tertiary Amines
    Kaper, Tobias
    Geik, Dennis
    Fornfeist, Felix
    Schmidtmann, Marc
    Doye, Sven
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (10)
  • [4] Titanium-catalyzed enantioselective synthesis of α-ambrinol
    Justicia, Jose
    Campana, Araceli G.
    Bazdi, Btissarn
    Robles, Rafael
    Cuerva, Juan M.
    Oltra, J. Enrique
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (04) : 571 - 576
  • [5] An enantioselective titanium-catalyzed synthesis of cyclopentenones.
    Hicks, FA
    Kablaoui, NM
    Buchwald, SL
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 213 : 636 - ORGN
  • [6] Highly Stereoselective Bronsted Acid Catalyzed Synthesis of Spirooxindole Pyrans
    Wang, Jingqi
    Crane, Erika A.
    Scheidt, Karl A.
    [J]. ORGANIC LETTERS, 2011, 13 (12) : 3086 - 3089
  • [7] Advances in Titanium-Catalyzed Synthesis of Chiral Sulfoxide Drugs
    Zeng, Qingle
    Gao, Shan
    Chelashaw, Allan Kipruto
    [J]. MINI-REVIEWS IN ORGANIC CHEMISTRY, 2013, 10 (02) : 198 - 206
  • [8] Synthesis of Chiral Drugs by Titanium-Catalyzed Enantioselective Sulfoxidation
    Gao Shan
    Zeng Qingle
    Tang Hongyan
    Liu Yang
    Dong Junyu
    Zhang Binbin
    [J]. PROGRESS IN CHEMISTRY, 2010, 22 (09) : 1760 - 1766
  • [9] Titanium-Catalyzed Hydroaminoalkylation of Ethylene
    Rosien, Michael
    Toeben, Iris
    Schmidtmann, Marc
    Beckhaus, Ruediger
    Doye, Sven
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (10) : 2138 - 2142
  • [10] Titanium-catalyzed iminohydrazination of alkynes
    Banerjee, S
    Shi, YH
    Cao, CS
    Odom, AL
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (23) : 5066 - 5077
12345