Direct Ruthenium-Catalyzed C-C Coupling of Ethanol: Diene Hydro-hydroxyethylation To Form All-Carbon Quaternary Centers

被引:39
作者
Han, Hoon [1 ]
Krische, Michael J. [1 ]
机构
[1] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA
关键词
ALDEHYDE OXIDATION LEVEL; TRANSFER HYDROGENATION; BOND FORMATION; BETA; GAMMA-UNSATURATED KETONES; UNACTIVATED OLEFINS; COMPLEX CATALYST; 1,3-DIENES; ALCOHOL; HOMOALLYLATION; ALLYLATION;
D O I
10.1021/ol101077v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Under ruthenium-catalyzed transfer hydrogenation conditions, direct C C coupling of ethanol and 2-substituted dienes occurs to furnish products of hydro-hydroxyethylation: anti-configured neopentyl homoallylic alcohols. Identical adducts are generated from acetaldehyde under related conditions employing isopropanol as reductant.
引用
收藏
页码:2844 / 2846
页数:3
相关论文
共 50 条
[31]  
Patman RL, 2008, ALDRICHIM ACTA, V41, P95
[32]   Direct Vinylation of Alcohols or Aldehydes Employing Alkynes as Vinyl Donors: A Ruthenium Catalyzed C-C Bond-Forming Transfer Hydrogenation [J].
Patman, Ryan L. ;
Chaulagain, Mani Raj ;
Williams, Vanessa M. ;
Krische, Michael J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (06) :2066-+
[33]   Formaldehyde synthesis from methanol over silver catalysts [J].
Qian, M ;
Liauw, MA ;
Emig, G .
APPLIED CATALYSIS A-GENERAL, 2003, 238 (02) :211-222
[34]   Nickel-catalyzed intermolecular coupling of 1,3-dienes and aldehydes via transmetalation of nickelacycles with diisobutylaluminum acetylacetonate [J].
Sato, Y ;
Sawaki, R ;
Saito, N ;
Mori, M .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (03) :656-662
[35]   Nickel-catalyzed enantio- and diastereoselective three-component coupling of 1,3-dienes, aldehydes, and silanes using chiral N-heterocyclic carbenes as ligands [J].
Sato, Yoshihiro ;
Hinata, Yu ;
Seki, Reiko ;
Oonishi, Yoshihiro ;
Saito, Nozomi .
ORGANIC LETTERS, 2007, 9 (26) :5597-5599
[36]   The E factor: fifteen years on [J].
Sheldon, Roger A. .
GREEN CHEMISTRY, 2007, 9 (12) :1273-1283
[37]   Diene Hydroacylation from the Alcohol or Aldehyde Oxidation Level via Ruthenium-Catalyzed C-C Bond-Forming Transfer Hydrogenation: Synthesis of β,γ-Unsaturated Ketones [J].
Shibahara, Fumitoshi ;
Bower, John F. ;
Krische, Michael J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (43) :14120-14122
[38]   Ruthenium-catalyzed C-C bond forming transfer hydrogenation: Carbonyl allylation from the alcohol or aldehyde oxidation level employing acyclic 1,3-dienes as surrogates to preformed allyl metal reagents [J].
Shibahara, Fumitoshi ;
Bower, John F. ;
Krische, Michael J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (20) :6338-+
[39]   Formation of C-C Bonds via Ruthenium-catalyzed Transfer Hydrogenation: Carbonyl Addition from the Alcohol or Aldehyde Oxidation Level [J].
Shibahara, Fumitoshi ;
Krische, Michael J. .
CHEMISTRY LETTERS, 2008, 37 (11) :1102-1107
[40]   anti-Aminoallylation of Aldehydes via Ruthenium-Catalyzed Transfer Hydrogenative Coupling of Sulfonamido Allenes: 1,2-Aminoalcohols [J].
Skucas, Eduardas ;
Zbieg, Jason R. ;
Krische, Michael J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (14) :5054-+