Synthesis of Phthalans Via Copper-Catalyzed Enantioselective Cyclization/Carboetherification of 2-Vinylbenzyl Alcohols

被引:26
作者
Chen, Dake [1 ]
Chemler, Sherry R. [1 ]
机构
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
基金
美国国家卫生研究院;
关键词
CARBOXYLIC-ACIDS; ALKENES; CARBOHETEROFUNCTIONALIZATION; 1,3-DIHYDROISOBENZOFURANS; FUNCTIONALIZATION; HETEROCYCLES; DERIVATIVES; FLUSPIDINE;
D O I
10.1021/acs.orglett.8b02766
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantiomerically enriched phthalans were synthesized efficiently via an enantioselective copper-catalyzed alkene carboetherification reaction. In this reaction, 2-vinyl-benzyl alcohols enantioselectively cyclize then couple with vinylarenes. The utility of the method was demonstrated by the enantioselective synthesis of (R)-fluspidine, a sigma(1) receptor ligand.
引用
收藏
页码:6453 / 6456
页数:4
相关论文
共 25 条
[1]   Enantioselective Copper-Catalyzed Carboetherification of Unactivated Alkenes [J].
Bovino, Michael T. ;
Liwosz, Timothy W. ;
Kendel, Nicole E. ;
Miller, Yan ;
Tyminska, Nina ;
Zurek, Eva ;
Chemler, Sherry R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (25) :6383-6387
[2]   Distinctive In Vivo Kinetics of the New σ1 Receptor Ligands (R)-(+)- and (S)-(-)-18F-Fluspidine in Porcine Brain [J].
Brust, Peter ;
Deuther-Conrad, Winnie ;
Becker, Georg ;
Patt, Marianne ;
Donat, Cornelius K. ;
Stittsworth, Shannon ;
Fischer, Steffen ;
Hiller, Achim ;
Wenzel, Barbara ;
Dukic-Stefanovic, Sladjana ;
Hesse, Swen ;
Steinbach, Joerg ;
Wuensch, Bernhard ;
Lever, Susan Z. ;
Sabri, Osama .
JOURNAL OF NUCLEAR MEDICINE, 2014, 55 (10) :1730-1736
[3]   Stereoselective and Regioselective Synthesis of Heterocycles via Copper-Catalyzed Additions of Amine Derivatives and Alcohols to Alkenes [J].
Chemler, Sherry R. ;
Karyakarte, Shuklendu D. ;
Khoder, Zainab M. .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (21) :11311-11325
[4]   An Enantioselective Approach toward 3,4-Dihydroisocoumarin through the Bromocyclization of Styrene-type Carboxylic Acids [J].
Chen, Jie ;
Zhou, Ling ;
Tan, Chong Kiat ;
Yeung, Ying-Yeung .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (02) :999-1009
[5]   Achiral Pyridine Ligand-Enabled Enantioselective Radical Oxytrifluoromethylation of Alkenes with Alcohols [J].
Cheng, Yong-Feng ;
Dong, Xiao-Yang ;
Gu, Qiang-Shuai ;
Yu, Zhang-Long ;
Liu, Xin-Yuan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (30) :8883-8886
[6]   Recent Developments in Pd0-Catalyzed Alkene-Carboheterofunctionalization Reactions [J].
Garlets, Zachary J. ;
White, Derick R. ;
Wolfe, John P. .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (06) :636-653
[7]  
HA TM, 2016, J CHEM SOC CHEM COMM, V52, P11100, DOI DOI 10.1039/C6CC06356J
[8]   Synthesis, Characterization, and Metabolism Studies of Fluspidine Enantiomers [J].
Holl, Katharina ;
Falck, Evamaria ;
Koehler, Jens ;
Schepmann, Dirk ;
Humpf, Hans-Ulrich ;
Brust, Peter ;
Wuensch, Bernhard .
CHEMMEDCHEM, 2013, 8 (12) :2047-2056
[9]   Development of Enantioselective Palladium-Catalyzed Alkene Carboalkoxylation Reactions for the Synthesis of Tetrahydrofurans [J].
Hopkins, Brett A. ;
Garlets, Zachary J. ;
Wolfe, John P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (45) :13390-13392
[10]   Synthesis of Chiral 1,4-Benzodioxanes and Chromans by Enantioselective Palladium-Catalyzed Alkene Aryloxyarylation Reactions [J].
Hu, Naifu ;
Li, Ke ;
Wang, Zheng ;
Tang, Wenjun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (16) :5044-5048