Enantioselective 1,1-Arylborylation of Alkenes: Merging Chiral Anion Phase Transfer with Pd Catalysis

被引：139
作者：
Nelson, Hosea M.
Williams, Brett D.
Miro, Javier
Toste, F. Dean [1 ]
机构：
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 09期
关键词：
ASYMMETRIC HYDROBORATION; FLUORINATION; ESTERS; CONSTRUCTION; ALLYLATION; STRATEGY; TERTIARY; LIGANDS; CARBON;
D O I：
10.1021/jacs.5b00344
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A palladium-catalyzed three-Component coupling of alpha-olefins, aryldiazonium salts, and bis-(pinacolato)diboron affords direct access to chiral benzylic boronic esters. This process is rendered highly enantioselective using an unprecedented example of cooperative chiral anion phase transfer and tiansition-metal catalysis.
引用
收藏
页码：3213 / 3216
页数：4
相关论文
共 41 条
[1]   Stereospecific reaction of α-carbamoyloxy-2-alkenylboronates and α-carbamoyloxy-alkylboronates with Grignard reagents -: Synthesis of highly enantioenriched secondary alcohols [J].
Beckmann, E ;
Desai, V ;
Hoppe, D .
SYNLETT, 2004, (13) :2275-2280
[2]   Asymmetric copper-catalyzed synthesis of α-amino boronate esters from N-tert-butanesulfinyl aldimines [J].
Beenen, Melissa A. ;
An, Chihui ;
Ellman, Jonathan A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (22) :6910-+
[3]   Asymmetric Ion-Pairing Catalysis [J].
Brak, Katrien ;
Jacobsen, Eric N. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (02) :534-561
[4]   Catalytic methodologies for the β-boration of conjugated electron deficient alkenes [J].
Calow, Adam D. J. ;
Whiting, Andrew .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (29) :5485-5497
[5]   The development of enantioselective rhodium-catalysed hydroboration of olefins [J].
Carroll, AM ;
O'Sullivan, TP ;
Guiry, PJ .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (05) :609-631
[6]   NHC-Cu-Catalyzed Enantioselective Hydroboration of Acyclic and Exocyclic 1,1-Disubstituted Aryl Alkenes [J].
Corberan, Rosa ;
Mszar, Nicholas W. ;
Hoveyda, Amir H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (31) :7079-7082
[7]   Catalytic asymmetric hydroboration: Recent advances and applications in carbon-carbon bond-forming reactions [J].
Crudden, CM ;
Edwards, D .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (24) :4695-4712
[8]   Stereoselective Preparation of β-Aryl-β-Boronyl Enoates and Their Copper-Catalyzed Enantioselective Conjugate Reduction [J].
Ding, Jinyue ;
Lee, Jack Chang Hung ;
Hall, Dennis G. .
ORGANIC LETTERS, 2012, 14 (17) :4462-4465
[9]   Regio- and Enantioselective Copper(I)-Catalyzed Hydroboration of Borylalkenes: Asymmetric Synthesis of 1,1-Diborylalkanes [J].
Feng, Xinhui ;
Jeon, Heekyung ;
Yun, Jaesook .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (14) :3989-3992
[10]   Enantioselective Synthesis of Allylboronates Bearing a Tertiary or Quaternary B-Substituted Stereogenic Carbon by NHC-Cu-Catalyzed Substitution Reactions [J].
Guzman-Martinez, Aikomari ;
Hoveyda, Amir H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (31) :10634-10637
12345