Asymmetric allylic substitution catalyzed by palladium-Yliphos complex

被引：30

作者：

Ohta, T ^{[1
]}

Sasayama, H ^{[1
]}

Nakajima, O ^{[1
]}

Kurahashi, N ^{[1
]}

Fujii, T ^{[1
]}

Furukawa, I ^{[1
]}

机构：

[1] Doshisha Univ, Fac Engn, Dept Mol Sci & Technol, Kyoto 6100394, Japan

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 05期

关键词：

D O I：

10.1016/S0957-4166(03)00046-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Allylic substitution reactions catalyzed by Pd- or Pt-Yliphos complexes are examined. The reaction of 1,3-diphenyl-2-propenyl acetate with benzylamine proceeded in the presence of Pd(dba)(2)-Yliphos to give N-benzyl-1,3-diphenyl-2-propenylamine in high yields with high enantioselectivities (up to 90% ee). Furthermore, the allylic alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate catalyzed by Pd-Yliphos complex resulted in high enantioselectivity (95% ee) in the presence of LiH as base. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：537 / 542

页数：6

共 34 条

[11]

Jacobsen E.N., 2000, Comprehensive Asymmetric Catalysis I-III (Eds)

[12]

Kagan H. B., 1978, TOP STEREOCHEM, V10, P175

[13] Palladium-catalyzed asymmetric reduction of racemic allylic esters with formic acid:: Effects of phosphine ligands on isomerization of π-allylpalladium intermediates and enantioselectivity [J].

Kawatsura, M ;

Uozumi, Y ;

Ogasawara, M ;

Hayashi, T .

TETRAHEDRON, 2000, 56 (15) :2247-2257

[14]

Kodama H, 2001, SYNLETT, P385

[15] Palladium-catalyzed asymmetric allylic substitution using novel phosphino-ester (PHEST) ligands with 1,1′-binaphthyl skeleton [J].

Kodama, H ;

Taiji, T ;

Ohta, T ;

Furukawa, I .

TETRAHEDRON-ASYMMETRY, 2000, 11 (19) :4009-4015

[16] The preparation of enantiomerically enriched γ-amino acids (GABAs) using palladium catalysed allylic substitution [J].

Martin, CJ ;

Rawson, DJ ;

Williams, JMJ .

TETRAHEDRON-ASYMMETRY, 1998, 9 (20) :3723-3730

[17]

MORRISON JD, 1993, ASYMMETRIC SYNTHESIS, V5, P2000

[18] Palladium-catalyzed asymmetric allylic substitution reactions using new chiral phosphinooxathiane ligands [J].

Nakano, H ;

Okuyama, Y ;

Yanagida, M ;

Hongo, H .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (02) :620-625

[19]

OHTA T, 1998, SCI ENG REV DOSHISHA, V39, P133

[20] Molecular mechanics predictions and experimental testing of asymmetric palladium-catalyzed allylation reactions using new chiral phenanthroline ligands [J].

PenaCabrera, E ;

Norrby, PO ;

Sjogren, M ;

Vitagliano, A ;

DeFelice, V ;

Oslob, J ;

Ishii, S ;

ONeill, D ;

Akermark, B ;

Helquist, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (18) :4299-4313

← 1 2 3 4 →