Et2Zn as a base:: zinc enolate free from other metals significantly enhances the enantiomeric excess in palladium-catalyzed allylic alkylation

被引:31
作者
Fuji, K [1 ]
Kinoshita, N
Tanaka, K
机构
[1] Kyoto Univ, Inst Chem Res, Kyoto 6110011, Japan
[2] Univ Shizuoka, Sch Pharmaceut Sci, Shizuoka 4228526, Japan
关键词
D O I
10.1039/a906034k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The enantiomeric excess of palladium-catalyzed allylic alkylations was greatly increased when Et2Zn was used as the base to generate an anion from malonates.
引用
收藏
页码:1895 / 1896
页数:2
相关论文
共 9 条
[1]   Acceleration of the conjugate addition of diethyl zinc to enones by either Cu(OTf)(2) or trivalent phosphorus ligands [J].
Alexakis, A ;
Vastra, J ;
Mangeney, P .
TETRAHEDRON LETTERS, 1997, 38 (44) :7745-7748
[2]  
CHARETTE AB, 1995, SYNLETT, P1197
[3]   Asymmetric ring opening reactions of symmetrical N-acylaziridines with thiols catalyzed by chiral dialkyltartrate-diethylzinc complexes [J].
Hayashi, M ;
Ono, K ;
Hoshimi, H ;
Oguni, N .
TETRAHEDRON, 1996, 52 (23) :7817-7832
[4]   Synthesis of cyclopropanols via cyclopropanation of zinc enolates [J].
Ito, S ;
Shinokubo, H ;
Oshima, K .
TETRAHEDRON LETTERS, 1998, 39 (29) :5253-5256
[5]   Novel carbonyl-dependent regioselective allylation via diethylzinc-mediated umpolung of π-allylpalladium [J].
Kimura, M ;
Ogawa, Y ;
Shimizu, M ;
Sueishi, M ;
Tanaka, S ;
Tamaru, Y .
TETRAHEDRON LETTERS, 1998, 39 (38) :6903-6906
[6]   Quantitative analysis of the chiral amplification in the amino alcohol-promoted asymmetric alkylation of aldehydes with dialkylzincs [J].
Kitamura, M ;
Suga, S ;
Oka, H ;
Noyori, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (38) :9800-9809
[7]   ANIONIC-POLYMERIZATION OF ALKYL METHACRYLATES IN THE PRESENCE OF DIETHYLZINC [J].
OZAKI, H ;
HIRAO, A ;
NAKAHAMA, S .
MACROMOLECULAR CHEMISTRY AND PHYSICS, 1995, 196 (07) :2099-2111
[8]   Asymmetric olefination of metallic arene or diene complexes to form planar chiral complexes [J].
Tanaka, K ;
Watanabe, T ;
Shimamoto, K ;
Sahakitpichan, P ;
Fuji, K .
TETRAHEDRON LETTERS, 1999, 40 (36) :6599-6602
[9]   PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC ALKYLATION USING DIMETHYL MALONATE AND ITS DERIVATIVES AS NUCLEOPHILE [J].
YAMAGUCHI, M ;
SHIMA, T ;
YAMAGISHI, T ;
HIDA, M .
TETRAHEDRON-ASYMMETRY, 1991, 2 (07) :663-666