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
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[1]   Green Chemistry: Principles and Practice [J].
Anastas, Paul ;
Eghbali, Nicolas .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) :301-312
[2]   First catalytic allyltitanation reactions [J].
Bareille, L ;
Le Gendre, P ;
Moïse, C .
CHEMICAL COMMUNICATIONS, 2005, (06) :775-777
[3]   Catalytic Carbonyl Addition through Transfer Hydrogenation: A Departure from Preformed Organometallic Reagents [J].
Bower, John F. ;
Kim, In Su ;
Patman, Ryan L. ;
Krische, Michael J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) :34-46
[4]   Green chemistry for the second generation biorefinery - sustainable chemical manufacturing based on biomass [J].
Clark, James H. .
JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, 2007, 82 (07) :603-609
[5]   Catalytic, enantioselective addition of substituted allylic trichlorosilanes using a rationally-designed 2,2′-bispyrrolidine-based bisphosphoramide [J].
Denmark, SE ;
Fu, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (38) :9488-9489
[6]  
Dérien S, 2004, TOP ORGANOMETAL CHEM, V11, P1
[7]  
DOBSON A, 1974, J CHEM SOC DA, P370
[8]   Regio- and Stereoselective Ni-Catalyzed 1,4-Hydroboration of 1,3-Dienes: Access to Stereodefined (Z)-Allylboron Reagents and Derived Allylic Alcohols [J].
Ely, Robert J. ;
Morken, James P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (08) :2534-+
[9]   Protecting-Group-Free Synthesis of 3-tert-Prenylated Oxindoles: Contiguous All-Carbon Quaternary Centers via Tertiary Neopentyl Substitution [J].
Grant, Christopher D. ;
Krische, Michael J. .
ORGANIC LETTERS, 2009, 11 (20) :4485-4487
[10]   Hydroaminoalkylation of Unactivated Olefins with Dialkylamines [J].
Herzon, Seth B. ;
Hartwig, John F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) :14940-+