Construction of 1,5-Enynes by Stereospecific Pd-Catalyzed Allyl- Propargyi Cross-Couplings

被引：48

作者：

Ardolino, Michael J. ^{[1
]}

Morken, James P. ^{[1
]}

机构：

[1] Boston Coll, Dept Chem, Merkert Chem Ctr, Chestnut Hill, MA 02467 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 21期

关键词：

ACID-PROMOTED CYCLIZATIONS; BOND-FORMING REACTIONS; NUCLEOPHILIC-SUBSTITUTION; REDUCTIVE ELIMINATION; ARYLBORONIC ACIDS; CONVENIENT METHOD; PALLADIUM; ALCOHOLS; COMPLEXES; ALLENES;

D O I：

10.1021/ja302329f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The palladium-catalyzed cross-coupling of chiral propargyl acetates and allyl boronates delivers chiral 1,5-enynes with excellent levels of chirality transfer and can be applied across a broad range of substrates.

引用

页码：8770 / 8773

页数：4

共 61 条

[1] eta(3)-Propargyl/allenyl complexes of platinum and palladium of the type [(PPh(3))(2)M(eta(3)-CH(2)CCR)](+) [J].

Baize, MW ;

Blosser, PW ;

Plantevin, V ;

Schimpff, DG ;

Gallucci, JC ;

Wojcicki, A .

ORGANOMETALLICS, 1996, 15 (01) :164-173

[2] Palladium(0) catalyzed regioselective carbonyl propargylation across tetragonal tin(II) oxide via redox transmetallation [J].

Banerjee, M ;

Roy, S .

CHEMICAL COMMUNICATIONS, 2003, (04) :534-535

[3]

Broger E.A., 1993, U.S. Patent, Patent No. 5274125

[4] Diastereocontrol in Asymmetric Allyl-Allyl Cross-Coupling: Stereocontrolled Reaction of Prochiral Allylboronates with Prochiral Allyl Chlorides [J].

Brozek, Laura A. ;

Ardolino, Michael J. ;

Morken, James P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (42) :16778-16781

[5] Mechanistic aspects of C-C bond formation involving allylpalladium complexes:: the role of computational studies [J].

Cárdenas, DJ ;

Echavarren, AM .

NEW JOURNAL OF CHEMISTRY, 2004, 28 (03) :338-347

[6] RELATIVE REACTIVITIES OF ALKYL CHLORIDES UNDER FRIEDEL-CRAFTS CONDITIONS [J].

DAUSCHMIDT, JP ;

MAYR, H .

CHEMISCHE BERICHTE, 1994, 127 (01) :205-212

[7] 1,5-enyne metathesis [J].

Debleds, Olivier ;

Campagne, Jean-Marc .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (05) :1562-+

[8] Synthesis of optically active allenes using tandem enzyme and palladium-catalysed reactions [J].

Dixneuf, PH ;

Guyot, T ;

Ness, MD ;

Roberts, SM .

CHEMICAL COMMUNICATIONS, 1997, (21) :2083-2084

[9] STEREOCHEMISTRY OF THE PD(PPH3)4-CATALYZED CONVERSION OF 1-BROMOALLENES INTO PHENYL SUBSTITUTED ALLENES [J].

ELSEVIER, CJ ;

MOOIWEER, HH ;

KLEIJN, H ;

VERMEER, P .

TETRAHEDRON LETTERS, 1984, 25 (48) :5571-5572

[10] ANTI STEREOSELECTIVITY IN THE PALLADIUM(0)-CATALYZED CONVERSION OF PROPARGYLIC ESTERS INTO ALLENES BY PHENYLZINC CHLORIDE [J].

ELSEVIER, CJ ;

STEHOUWER, PM ;

WESTMIJZE, H ;

VERMEER, P .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (07) :1103-1105

← 1 2 3 4 5 6 7 →