Novel ferrocenyl ligands with planar and central chirality in Pd-catalyzed allylic substitutions

被引：58

作者：

Enders, D ^{[1
]}

Peters, R ^{[1
]}

Runsink, J ^{[1
]}

Bats, JW ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 11期

关键词：

D O I：

10.1021/ol991139l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The use of planar chiral ferrocenyl ligands bearing a stereogenic center in beta-position of the side chain was investigated in Pd-catalyzed enantioselective allylic substitutions. By employing 2.2 mol % of a P,S-ligand and 1.0 mol % of [Pd(eta(3)-C3H5)Cl](2), the alkylation of the standard test system (+/-) (E)-diphenyl-2-propenyl acetate using dimethylmalonate/BSA as nucleophile proceeded in quantitative yield with an ee of 97%, which is the best value reported so far in this reaction using a P,S-ligand.

引用

页码：1863 / 1866

页数：4

共 50 条

[21] New [5]ferrocenophane diphosphine ligands for Pd-catalyzed allylic substitution
Sebesta, Radovan
Almassy, Ambroz
Gisarova, Ivana
Toma, Stefan
TETRAHEDRON-ASYMMETRY, 2006, 17 (17) : 2531 - 2537
[22] Diphenylphosphinooxazoline ligands with a chiral binaphthyl backbone for Pd-catalyzed allylic alkylation
Imai, Y
Zhang, WB
Kida, T
Nakatsuji, Y
Ikeda, I
TETRAHEDRON LETTERS, 1998, 39 (24) : 4343 - 4346
[23] Modular furanoside phosphite ligands for asymmetric pd-catalyzed allylic substitution
Pàmies, O
van Strijdonck, GPF
Diéguez, M
Deerenberg, S
Net, G
Ruiz, A
Claver, C
Kamer, PCJ
van Leeuwen, PWNM
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26): : 8867 - 8871
[24] New ligands for regio- and enantiocontrol in Pd-catalyzed allylic alkylations
Prétôt, R
Pfaltz, A
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1998, 37 (03) : 323 - 325
[25] Pd-catalyzed asymmetric allylic alkylation using furanoside diphosphinite ligands
Guimet, E
Diéguez, M
Ruiz, A
Claver, C
INORGANICA CHIMICA ACTA, 2005, 358 (13) : 3824 - 3828
[26] Ferrocenylphosphine-imine ligands for Pd-catalyzed asymmetric allylic alkylation
Hu, XP
Dai, HG
Hu, XU
Chen, HL
Wang, JW
Bai, CM
Zheng, Z
TETRAHEDRON-ASYMMETRY, 2002, 13 (15) : 1687 - 1693
[27] Role of planar chirality of S,N- and P,N-ferrocene ligands in palladium-catalyzed allylic substitutions
You, SL
Hou, XL
Dai, LX
Yu, YH
Xia, W
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14): : 4684 - 4695
[28] Importance of planar chirality in chiral catalysts with three chiral elements:: The role of planar chirality in 2′-substituted 1,1′-P,N-Ferrocene ligands on the enantioselectivity in Pd-catalyzed allylic substitution
Deng, WP
You, SL
Hou, XL
Dai, LX
Yu, YH
Xia, W
Sun, J
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (27) : 6508 - 6519
[29] Pd-catalyzed allylic alkylation of thioamides
Rong, Bin
Ding, Lei
Yu, Hailei
Yang, Qin
Liu, Xuliang
Xu, Dongfang
Li, Guisheng
Zhao, Baoguo
TETRAHEDRON LETTERS, 2013, 54 (48) : 6501 - 6503
[30] Memory and dynamics in Pd-catalyzed allylic alkylation with P,N-ligands
Johansson, Charlotte
Lloyd-Jones, Guy C.
Norrby, Per-Ola
TETRAHEDRON-ASYMMETRY, 2010, 21 (11-12) : 1585 - 1592

← 1 2 3 4 5 →