Chiral Phosphaalkene-Oxazoline Ligands for the Palladium-Catalyzed Asymmetric Allylic Alkylation

被引：42

作者：

Dugal-Tessier, Julien ^{[1
]}

Dake, Gregory R. ^{[1
]}

Gates, Derek P. ^{[1
]}

机构：

[1] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 20期

基金：

加拿大自然科学与工程研究理事会;

关键词：

BEARING DIPHOSPHINIDENECYCLOBUTENE LIGANDS; HIGHLY-ACTIVE CATALYSTS; ETHYLENE POLYMERIZATION; COORDINATION CHEMISTRY; AZOMETHINE IMINES; TERMINAL ALKYNES; COMPLEXES; HETEROCYCLES; 5,5-DIMETHYL-4-ISO-PROPYLOXAZOLIDIN-2-ONE; PERSPECTIVES;

D O I：

10.1021/ol1020652

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective catalysis in moderate to excellent yields and ee's has been accomplished using a phosphaalkene-based ligand system. Specifically, the palladium-catalyzed allylic alkylation of 1,3-diphenyl-2-propenyl acetate using a chiral P(sp(2)),N(sp(2)) ligand proceeds with a variety of malonate nucleophiles in 73-95% yield (79-92% ee).

引用

页码：4667 / 4669

页数：3

共 41 条

[1]

AUSIERI M, 2008, CHEM-EUR J, V14, P5737

[2] Phospha-organic chemistry: from molecules to polymers [J].

Bates, Joshua I. ;

Dugal-Tessier, Julien ;

Gates, Derek P. .

DALTON TRANSACTIONS, 2010, 39 (13) :3151-3159

[3] Use of 5,5-(Dimethyl)-i-Pr-PHOX as a Practical Equivalent to t-Bu-PHOX in Asymmetric Catalysis [J].

Belanger, Etienne ;

Pouliot, Marie-France ;

Paquin, Jean-Francois .

ORGANIC LETTERS, 2009, 11 (10) :2201-2204

[4]

BIETT B, 2001, CHEM-EUR J, V7, P3106

[5] New developments in stereoselective palladium-catalyzed allylic alkylations of preformed enolates [J].

Braun, M ;

Meier, T .

SYNLETT, 2006, (05) :661-676

[6] Conformational control in the SuperQuat chiral auxiliary 5,5-dimethyl-4-iso-propyloxazolidin-2-one induces the iso-propyl group to mimic a tert-butyl group [J].

Bull, SD ;

Davies, SG ;

Key, MS ;

Nicholson, RL ;

Savory, ED .

CHEMICAL COMMUNICATIONS, 2000, (18) :1721-1722

[7] SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one [J].

Bull, Steven D. ;

Davies, Stephen G. ;

Garner, A. Christopher ;

Kruchinin, Dennis ;

Key, Min-Suk ;

Roberts, Paul M. ;

Savory, Edward D. ;

Smith, Andrew D. ;

Thomson, James E. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (15) :2945-2964

[8] Phosphinidine-palladium complexes for the polymerization and oligomerization of ethylene [J].

Daugulis, O ;

Brookhart, M ;

White, PS .

ORGANOMETALLICS, 2002, 21 (26) :5935-5943

[9] ASYMMETRIC PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION USING PHOSPHORUS-CONTAINING OXAZOLINE LIGANDS [J].

DAWSON, GJ ;

FROST, CG ;

WILLIAMS, JMJ .

TETRAHEDRON LETTERS, 1993, 34 (19) :3149-3150

[10] Chiral Ligand Design: A Bidentate Ligand Incorporating an Acyclic Phosphaalkene [J].

Dugal-Tessier, Julien ;

Dake, Gregory R. ;

Gates, Derek P. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (42) :8064-8067

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