Steric effects of the ligand in the enantioselective palladium-catalyzed allylic alkylation using chiral oxazolinylpyridines

被引：46

作者：

Chelucci, G ^{[1
]}

Medici, S ^{[1
]}

Saba, A ^{[1
]}

机构：

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

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 03期

关键词：

D O I：

10.1016/S0957-4166(99)00023-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Eight new chiral oxazolinylpyridines were prepared and assessed in the enantioselective palladium-catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate. Catalytic activity and enantioselectivity were found to be highly dependent upon the steric requirement of the substituent on the pyridine ring: enantioselectivity up to 92% has been obtained. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：543 / 550

页数：8

共 16 条

[1] First-principles investigation of enantioselective catalysis: Asymmetric allylic amination with Pd complexes bearing P,N-ligands
Blochl, PE
Togni, A
[J]. ORGANOMETALLICS, 1996, 15 (20) : 4125 - 4132
[2] SYNTHESIS OF OPTICALLY-ACTIVE BIS(2-OXAZOLINES) - CRYSTAL-STRUCTURE OF A 1,2-BIS(2-OXAZOLINYL)BENZENE.ZNCL2 COMPLEX
BOLM, C
WEICKHARDT, K
ZEHNDER, M
RANFF, T
[J]. CHEMISCHE BERICHTE, 1991, 124 (05) : 1173 - 1180
[3] ASYMMETRIC CATALYSIS .45. ENANTIOSELECTIVE HYDROSILYLATION OF KETONES WITH [RH(COD)CL]2/PYRIDINYLOXAZOLINE CATALYSTS
BRUNNER, H
OBERMANN, U
[J]. CHEMISCHE BERICHTE-RECUEIL, 1989, 122 (03): : 499 - 507
[4] New chiral C-2-symmetric bis(oxazolinylpyridinyl)dioxolane ligands for asymmetric catalysis: palladium catalysed allylic substitution
Chelucci, G
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (16) : 2667 - 2670
[5] Chiral oxazolinylpyridines as ligands for enantioselective palladium catalysed allylic substitution
Chelucci, G
Medici, S
Saba, A
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (19) : 3183 - 3184
[6] COLONNA M, 1953, GAZZ CHIM ITAL, V83, P623
[7] REGIOSELECTIVE CYANATION OF PYRIDINE 1-OXIDES WITH TRIMETHYLSILANECARBONITRILE - A MODIFIED REISSERT-HENZE REACTION
FIFE, WK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (08) : 1375 - 1377
[8] SELECTIVITY IN PALLADIUM CATALYZED ALLYLIC SUBSTITUTION
FROST, CG
HOWARTH, J
WILLIAMS, JMJ
[J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (09) : 1089 - 1122
[9] HAYASHI T, 1993, CATALYTIC ASYMMETRIC
[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

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