Water-accelerated tandem Claisen rearrangement-catalytic asymmetric carboalumination

被引:40
作者
Wipf, P [1 ]
Ribe, S [1 ]
机构
[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
关键词
D O I
10.1021/ol015816z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The addition of stoichiometric quantities of water accelerates both the trimethylaluminum mediated aromatic Claisen reaction and the chiral zirconocene-catalyzed asymmetric carboalumination of terminal alkenes, The two reactions occur in a tandem sequence resulting in the selective formation of two new C-C and one C-O bond after oxidative quench of the intermediate trialkylalane.
引用
收藏
页码:1503 / 1505
页数:3
相关论文
共 12 条
[1]   LEWIS ACID-PROMOTED 3-AZA-COPE REARRANGEMENT OF N-ALKYL-N-ALLYLANILINES [J].
BEHOLZ, LG ;
STILLE, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) :5095-5100
[2]   Cocatalysts for metal-catalyzed olefin polymerization: Activators, activation processes, and structure-activity relationships [J].
Chen, EYX ;
Marks, TJ .
CHEMICAL REVIEWS, 2000, 100 (04) :1391-1434
[3]   THE ROLE OF TORSIONAL ISOMERS OF PLANARLY CHIRAL NONBRIDGED BIS(INDENYL)METAL TYPE COMPLEXES IN STEREOSELECTIVE PROPENE POLYMERIZATION [J].
ERKER, G ;
AULBACH, M ;
KNICKMEIER, M ;
WINGBERMUHLE, D ;
KRUGER, C ;
NOLTE, M ;
WERNER, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (11) :4590-4601
[4]   ZIRCONIUM-CATALYZED ENANTIOSELECTIVE METHYLALUMINATION OF MONOSUBSTITUTED ALKENES [J].
KONDAKOV, DY ;
NEGISHI, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (43) :10771-10772
[5]   CATALYSIS OF THE COPE AND CLAISEN REARRANGEMENTS [J].
LUTZ, RP .
CHEMICAL REVIEWS, 1984, 84 (03) :205-247
[6]   MOLECULAR DESIGN OF A CHIRAL LEWIS-ACID FOR THE ASYMMETRIC CLAISEN REARRANGEMENT [J].
MARUOKA, K ;
SAITO, S ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (03) :1165-1166
[7]   Optical rotation computation, total synthesis, and stereochemistry assignment of the marine natural product pitiamide A [J].
Ribe, S ;
Kondru, RK ;
Beratan, DN ;
Wipf, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (19) :4608-4617
[8]  
Sharma GVM, 2000, SYNLETT, P615
[9]   RAPID CARBOALUMINATION OF ALKYNES IN THE PRESENCE OF WATER [J].
WIPF, P ;
LIM, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (07) :1068-1071
[10]   Water/MAO acceleration of the zirconocene-catalyzed asymmetric methylalumination of α-olefins [J].
Wipf, P ;
Ribe, S .
ORGANIC LETTERS, 2000, 2 (12) :1713-1716