Chiral P-Containing Palladacycle-Catalyzed Asymmetric Ring-Opening Reactions of Oxabicyclic Alkenes with Alkenyl Boronic Acids

被引：30

作者：

Huang, Xiao-Jun ^{[1
]}

Mo, Dong-Liang ^{[1
]}

Ding, Chang-Hua ^{[1
]}

Hou, Xue-Long ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

SYNLETT | 2011年 / 07期

基金：

中国国家自然科学基金;

关键词：

palladacycle; asymmetric catalysis; ring-opening reaction; oxabicyclic alkenes; alkenyl boronic acids; AZA-CLAISEN REARRANGEMENT; ALLYLIC AMINES; ENANTIOSELECTIVE CATALYSTS; CYCLOPALLADATED COMPLEXES; ARYLBORONIC ACIDS; C-C; PALLADIUM; LIGANDS; HECK; 1,4-ADDITION;

D O I：

10.1055/s-0030-1259716

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient palladacycle-catalyzed asymmetric ring-opening reaction of oxabicyclic alkenes with alkenyl boronic acids was developed to afford the corresponding products in good to excellent yields and enantioselectivity.

引用

收藏

页码：943 / 946

页数：4

相关论文

共 63 条

[1]

ALBRECHT M, 2000, J ORGANOMET CHEM, V19, P1282

[2] Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity [J].

Anderson, CE ;

Overman, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (41) :12412-12413

[3] Catalytic asymmetric synthesis of chiral allylic amines. Evaluation of ferrocenyloxazoline palladacycle catalysts and imidate motifs [J].

Anderson, CE ;

Donde, Y ;

Douglas, CJ ;

Overman, LE .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) :648-657

[4] Palladacyclic catalysts in C-C and C-heteroatom bond-forming reactions [J].

Bedford, RB .

CHEMICAL COMMUNICATIONS, 2003, (15) :1787-1796

[5] Palladacycles in catalysis - a critical survey [J].

Beletskaya, IP ;

Cheprakov, AV .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (24) :4055-4082

[6] SYNTHESIS OF BIS-CYCLOMETALLATING N-C-N HEXADENTATE LIGANDS VIA C-C AROMATIC COUPLINGS AND THEIR DINUCLEAR RUTHENIUM(II) COMPLEXES [J].

BELEY, M ;

CHODOROWSKI, S ;

COLLIN, JP ;

SAUVAGE, JP .

TETRAHEDRON LETTERS, 1993, 34 (18) :2933-2936

[7] Copper phosphoramidite catalyzed enantioselective ring-opening of oxabicyclic alkenes: Remarkable reversal of stereocontrol [J].

Bertozzi, F ;

Pineschi, M ;

Macchia, F ;

Arnold, LA ;

Minnaard, AJ ;

Feringa, BL .

ORGANIC LETTERS, 2002, 4 (16) :2703-2705

[8] Chiral cyclopalladated complexes derived from N,N-dimethyl-1-phenethylamine with bridging bis(diphenylphosphine)ferrocene ligand as inhibitors of the cathepsin B activity and as antitumoral agents [J].

Bincoletto, C ;

Tersariol, ILS ;

Oliveira, CR ;

Dreher, S ;

Fausto, DM ;

Soufen, MA ;

Nascimento, FD ;

Caires, ACF .

BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (08) :3047-3055

[9] Synthesis, characterization and catalytic activity in Heck-type reactions of orthometallated PdII and PtII complexes derived from (1R,2R)-1,2-diaminocyclohexane [J].

Bravo, J ;

Cativiela, C ;

Navarro, R ;

Urriolabeitia, EP .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 650 (1-2) :157-172

[10] Fesulphos-palladium(II) complexes as well-defined catalysts for enantioselective ring opening of meso heterobicyclic alkenes with organozinc reagents [J].

Cabrera, S ;

Arrayás, RG ;

Alonso, I ;

Carretero, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (50) :17938-17947

← 1 2 3 4 5 6 7 →