Cyclopenta[b]thiophene-alkyloxazolines:: new nitrogen-sulfur hybrid ligands and their use in asymmetric palladium-catalyzed allylic alkylation

被引：10

作者：

Bonini, BF

Giordano, L

Fochi, M

Comes-Franchini, M

Bernardi, L

Capitò, E

Ricci, A

机构：

[1] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy

[2] Fac Sci & Tech St Jerome, CNRS, Lab Synthese Asymetr, UMR 6516, F-13397 Marseille, France

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 06期

关键词：

D O I：

10.1016/j.tetasy.2004.01.036

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

New chiral nitrogen and sulfur containing hybrid ligands have been prepared and fully characterized. Their structure includes cyclopenta[b]tiophene and oxazoline moieties as sources of chirality. Their catalytic activity has been tested successfully in the Pd-allylic alkylation leading to enantioselectivities of up to 74% ee. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：1043 / 1051

页数：9

共 40 条

[11] SULFIDES TETHERED TO OXAZOLINES - LIGANDS FOR ENANTIOSELECTIVE CATALYSIS [J].

DAWSON, GJ ;

FROST, CG ;

MARTIN, CJ ;

WILLIAMS, JMJ .

TETRAHEDRON LETTERS, 1993, 34 (48) :7793-7796

[12] An improved procedure for the preparation of 2,2-bis[2-[4(S)-tert-butyl-1,3-oxazolinyl]]propane [(S,S)-tert-butylbis(oxazoline)] and derived copper(II) complexes [J].

Evans, DA ;

Peterson, GS ;

Johnson, JS ;

Barnes, DM ;

Campos, KR ;

Woerpel, KA .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (13) :4541-4544

[13] Nitrogen-containing ligands for asymmetric homogeneous and heterogeneous catalysis [J].

Fache, F ;

Schulz, E ;

Tommasino, ML ;

Lemaire, M .

CHEMICAL REVIEWS, 2000, 100 (06) :2159-2231

[14] ENANTIOSELECTIVE PALLADIUM CATALYZED ALLYLIC SUBSTITUTION WITH THIENYL OXAZOLINE LIGANDS [J].

FROST, CG ;

WILLIAMS, JMJ .

TETRAHEDRON LETTERS, 1993, 34 (12) :2015-2018

[15] C2-symmetric chiral bis(oxazoline)-metal complexes in catalytic asymmetric synthesis [J].

Ghosh, AK ;

Packiarajan, M ;

Cappiello, J .

TETRAHEDRON-ASYMMETRY, 1998, 9 (01) :1-45

[16] Catalytic asymmetric reactions via π-allylpalladium complexes coordinated with chiral monophosphine ligands [J].

Hayashi, T .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :195-202

[17]

Heller D, 2000, ANGEW CHEM INT EDIT, V39, P495, DOI 10.1002/(SICI)1521-3773(20000204)39:3<495::AID-ANIE495>3.0.CO

[18]

2-G

[19] Enantioselective palladium-catalyzed allylic substitutions with asymmetric chiral ligands [J].

Helmchen, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :203-214

[20] Nonlinear effects in the enantioselective 1,4-conjugate addition of diethylzinc to chalcone [J].

Hu, YC ;

Liang, XM ;

Zheng, Z ;

Hu, XQ .

TETRAHEDRON-ASYMMETRY, 2003, 14 (18) :2771-2774

← 1 2 3 4 →