Enantioselective palladium-catalyzed allylic substitutions with asymmetric chiral ligands

被引：310

作者：

Helmchen, G ^{[1
]}

机构：

[1] Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1999年 / 576卷 / 1-2期

关键词：

palladium; pi-allyl complexes; catalysis; asymmetric synthesis; phosphines;

D O I：

10.1016/S0022-328X(98)01059-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Phosphinooxazolines are highly effective ligands in Pd catalyzed asymmetric substitutions of allylic compounds. Malonates, amines and nitronates can be employed successfully as nucleophiles. Mechanistic aspects, studied by NMR and X-ray crystal structure analyses, are presented. These studies were focused on identification of Pd-bound intermediates in order to gain a clear understanding of the enantioselective step in the catalytic cycle. Also described are reactions under catalysis with Pd complexes of a new phosphinocarboxylic acid. Applications in syntheses of physiologically active compounds are presented. (C) 1999 Elsevier Science S.A. All rights reserved.

引用

页码：203 / 214

页数：12

共 59 条

[1] PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC SUBSTITUTION - A LIGAND DESIGN INCORPORATING STERIC AND ELECTRONIC EFFECTS
ALLEN, JV
COOTE, SJ
DAWSON, GJ
FROST, CG
MARTIN, CJ
WILLIAMS, JMJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (15): : 2065 - 2072
[2] ATKINS KE, 1970, TETRAHEDRON LETT, P3821
[3] ASYMMETRIC CATALYTIC ALLYLIC ALKYLATION
BOSNICH, B
MACKENZIE, PB
[J]. PURE AND APPLIED CHEMISTRY, 1982, 54 (01) : 189 - 195
[4] AN UNUSUAL, SELECTIVE ETA(3)-ETA(1) ALLYL ISOMERIZATION IN A CHIRAL ALLYLIC ALKYLATION CATALYST
BREUTEL, C
PREGOSIN, PS
SALZMANN, R
TOGNI, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (09) : 4067 - 4068
[5] MECHANISTIC AND SYNTHETIC STUDIES IN CATALYTIC ALLYLIC ALKYLATION WITH PALLADIUM COMPLEXES OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE
BROWN, JM
HULMES, DI
GUIRY, PJ
[J]. TETRAHEDRON, 1994, 50 (15) : 4493 - 4506
[6] CARMONA D, 1997, J CHEM SOC CHEM COMM, P2351
[7] NUCLEAR-MAGNETIC-RESONANCE AND CRYSTALLOGRAPHIC STUDIES OF CHIRAL ETA-3-ALLYL PALLADIUM(II) COMPLEXES AND ASYMMETRIC ALLYLIC ALKYLATION OF PROPEN-2-YL ACETATES
CESAROTTI, E
GRASSI, M
PRATI, L
DEMARTIN, F
[J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1991, (08): : 2073 - 2080
[8] COTOE SJ, 1993, SYNLETT, P509
[9] SULFIDES TETHERED TO OXAZOLINES - LIGANDS FOR ENANTIOSELECTIVE CATALYSIS
DAWSON, GJ
FROST, CG
MARTIN, CJ
WILLIAMS, JMJ
[J]. TETRAHEDRON LETTERS, 1993, 34 (48) : 7793 - 7796
[10] ASYMMETRIC PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION USING PHOSPHORUS-CONTAINING OXAZOLINE LIGANDS
DAWSON, GJ
FROST, CG
WILLIAMS, JMJ
[J]. TETRAHEDRON LETTERS, 1993, 34 (19) : 3149 - 3150

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