Homogeneous Pd-catalyzed enantioselective decarboxylative protonation

被引:69
作者
Marinescu, Smaranda C. [1 ]
Nishimata, Toyoki [1 ]
Mohr, Justin T. [1 ]
Stoltz, Brian M. [1 ]
机构
[1] CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
关键词
D O I
10.1021/ol702821j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
General homogeneous conditions for the palladium-catalyzed synthesis of carbonyl compounds with tertiary carbon stereocenters at the alpha-position are reported. The highly reactive catalyst tolerates a variety of substrate substitution and-functionality, and generates enantioenriched cyclic ketones from racemic allyl beta-ketoester starting materials.
引用
收藏
页码:1039 / 1042
页数:4
相关论文
共 35 条
[1]   PALLADIUM-MEDIATED ENANTIOSELECTIVE FORMATION OF 2-METHYLTETRAL-1-ONE FROM THE CORRESPONDING ALLYL OR BENZYL ENOL CARBONATE IN THE PRESENCE OF ENANTIOPURE AMINOALCOHOLS [J].
ABOULHODA, SJ ;
LETINOIS, S ;
WILKEN, J ;
REINERS, I ;
HENIN, F ;
MARTENS, J ;
MUZART, J .
TETRAHEDRON-ASYMMETRY, 1995, 6 (08) :1865-1868
[2]   PRODUCTION OF OPTICALLY-ACTIVE KETONES BY A PALLADIUM-INDUCED CASCADE REACTION FROM RACEMIC BETA-KETOESTERS [J].
ABOULHODA, SJ ;
HENIN, F ;
MUZART, J ;
THOREY, C ;
BEHNEN, W ;
MARTENS, J ;
MEHLER, T .
TETRAHEDRON-ASYMMETRY, 1994, 5 (07) :1321-1326
[3]   Highly enantioselective decarboxylative protonation of α-aminomalonates mediated by thiourea Cinchona alkaloid derivatives:: Access to both enantiomers of cyclic and acyclic α-aminoacids [J].
Amere, Mukkanti ;
Lasne, Marie-Claire ;
Rouden, Jacques .
ORGANIC LETTERS, 2007, 9 (14) :2621-2624
[4]  
[Anonymous], COMPREHENSIVE ASYMME
[5]   Catalytic asymmetric protonation of fluoro-enolic species:: access to optically active 2-fluoro-1-tetralone [J].
Baur, MA ;
Riahi, A ;
Hénin, F ;
Muzart, J .
TETRAHEDRON-ASYMMETRY, 2003, 14 (18) :2755-2761
[6]   The enantioselective Tsuji allylation [J].
Behenna, DC ;
Stoltz, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15044-15045
[7]   Meldrum's acid [J].
Bonifácio, VDB .
SYNLETT, 2004, (09) :1649-1650
[8]   INTRODUCTION OF OXYGEN FUNCTIONS INTO THE ALPHA-POSITION OF BETA-DIKETONES .4. HYDROXY-MELDRUMS AND OXO-MELDRUMS ACIDS [J].
BOUILLON, G ;
SCHANK, K .
CHEMISCHE BERICHTE-RECUEIL, 1980, 113 (08) :2630-2635
[9]   THE STRUCTURE OF MELDRUMS SUPPOSED BETA-LACTONIC ACID [J].
DAVIDSON, D ;
BERNHARD, SA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (10) :3426-3428
[10]   Enantioselective partial reduction of 2,5-disubstituted pyrroles via a chiral protonation approach [J].
Donohoe, TJ ;
Freestone, GC ;
Headley, CE ;
Rigby, CL ;
Cousins, RPC ;
Bhalay, G .
ORGANIC LETTERS, 2004, 6 (18) :3055-3058