1,10-phenanthrolines derived from natural occurring ketones as ligands for asymmetric catalysis: enantioselective palladium catalyzed allylic substitution

被引：37

作者：

Chelucci, G

Pinna, GA

Saba, A

Sanna, G

机构：

[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy

[2] Univ Sassari, Dipartimento Farmaco Chim Tossicol, I-07100 Sassari, Italy

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2000年 / 159卷 / 02期

关键词：

chiral 1,10-phenanthroline; palladium complex; allylic substitution; enantioselectivity;

D O I：

10.1016/S1381-1169(00)00210-7

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A number of chiral C-1-symmetric 1,10-phenanthrolines derived from naturally occurring ketones were assessed in the enantioselective palladium catalyzed allylic alkylation of 1,3-diphenylprop-2-enyl acetate with dimethylmalonate. Enantioselectivity up to 96% was obtained with a new 1,10-phenanthroline derived from 5 alpha-cholestan-4-one. (C) 2000 Elsevier Science B.V. All rights reserved.

引用

页码：423 / 427

页数：5

共 17 条

[1] Sterically hindered phenanthrolines: Synthesis of 1,7,7-trimethyl[2.2.1]bicycloheptano-[2,3-B]-1,10-phenanthroline from (+)-camphor.
Chelucci, G
Thummel, RP
[J]. SYNTHETIC COMMUNICATIONS, 1999, 29 (10) : 1665 - 1669
[2] Enantioselective palladium catalyzed allylic substitution with chiral pyridine ligands
Chelucci, G
Caria, V
Saba, A
[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1998, 130 (1-2) : 51 - 55
[3] Steric effects of the ligand in the enantioselective palladium-catalyzed allylic alkylation using chiral oxazolinylpyridines
Chelucci, G
Medici, S
Saba, A
[J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (03) : 543 - 550
[4] New 1,10-phenanthroline ligands for asymmetric catalysis: enantioselective palladium catalyzed allylic substitution
Chelucci, G
Saba, A
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (15) : 2575 - 2578
[5] Chiral pyridylmethyl- and quinolinyl-oxazolines as ligands for enantioselective palladium-catalyzed allylic alkylation
Chelucci, G
Gladiali, S
Saba, A
[J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (07) : 1393 - 1400
[6] CHELUCCI G, UNPUB
[7] SELECTIVITY IN PALLADIUM CATALYZED ALLYLIC SUBSTITUTION
FROST, CG
HOWARTH, J
WILLIAMS, JMJ
[J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (09) : 1089 - 1122
[8] Synthesis of phosphino oxazoline ligand libraries from amino acid and phosphino carboxylate building blocks
Gilbertson, SR
Chang, CWT
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) : 8424 - 8431
[9] HASAN M, 1995, LIEBIGS ANN, P1871
[10] Chiral nonracemic pyridine thiols and thioethers applied in palladium-catalyzed allylic substitution. An example of near-perfect enantioselection
Koning, B
Meetsma, A
Kellogg, RM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (16) : 5533 - 5540

← 1 2 →