Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones

被引:1112
作者
Denmark, SE [1 ]
Fu, JP [1 ]
机构
[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
关键词
D O I
10.1021/cr020050h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Excellent progress was made over past decade in the develoment, understanding, and application of catalytic, enantioselective allylation reactions. For simple allylation, good methods were available, but they require the use of toxic tin reagents and high loadings of the catalyst. For addition of substituted allylic residues, the problem of predictable and selective diastereocontrol was not solved in general. With Lewis acid-catalyzed reactions and insitu generation of allylic organometallic species, there were selective cases but also wide variability.
引用
收藏
页码:2763 / 2793
页数:31
相关论文
共 180 条
[1]   Stereoselective synthesis of 4-alkoxy-3-methylidenealkanols using reactions between 2-(1-alkoxyalkyl)propenylstannanes and aldehydes: X-ray crystal structure of (1R,4R)-3-methylidene-1-(4-nitrophenyl)pentane-1,4-diol [J].
Almendros, P ;
Gruttadauria, M ;
Helliwell, M ;
Thomas, EJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (17) :2549-2560
[2]  
Angell RM, 1997, CHEM COMMUN, P919
[3]  
[Anonymous], MODERN CARBONYL CHEM
[4]   ENANTIOSELECTIVE AND DIASTEREOSELECTIVE CATALYSIS OF ADDITION-REACTION OF ALLYLIC SILANES AND STANNANES TO GLYOXYLATES BY BINAPHTHOL-DERIVED TITANIUM COMPLEX [J].
AOKI, S ;
MIKAMI, K ;
TERADA, M ;
NAKAI, T .
TETRAHEDRON, 1993, 49 (09) :1783-1792
[5]  
Bandini M, 1999, ANGEW CHEM INT EDIT, V38, P3357, DOI 10.1002/(SICI)1521-3773(19991115)38:22<3357::AID-ANIE3357>3.0.CO
[6]  
2-W
[7]   Asymmetric synthesis with "privileged" ligands [J].
Bandini, M ;
Cozzi, PG ;
Umani-Ronchi, A .
PURE AND APPLIED CHEMISTRY, 2001, 73 (02) :325-329
[8]  
Bandini M, 2000, EUR J ORG CHEM, V2000, P491, DOI 10.1002/(SICI)1099-0690(200002)2000:3<491::AID-EJOC491>3.0.CO
[9]  
2-N
[10]   Cr(Salen)-catalyzed addition of 1,3-dichloropropene to aromatic aldehydes, a simple access to optically active vinyl epoxides [J].
Bandini, M ;
Cozzi, PG ;
Melchiorre, P ;
Morganti, S ;
Umani-Ronchi, A .
ORGANIC LETTERS, 2001, 3 (08) :1153-1155