Three-component enantioselective synthesis of propargylamines through Zr-catalyzed additions of alkyl zinc reagents to alkynylimines

被引：129

作者：

Akullian, LC ^{[1
]}

Snapper, ML ^{[1
]}

Hoveyda, AH ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 35期

关键词：

alkyl zinc reagents; asymmetric catalysis; enantioselectivity; propargylamines; zirconium;

D O I：

10.1002/anie.200352081

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Readily available amino acid based chiral ligands are used in a three-component Zr-catalyzed enantioselective synthesis of propargylamines (see schemes). The reaction affords important enantiomerically enriched building blocks that are not conveniently accessible by alternative catalytic methods.

引用

页码：4244 / 4247

页数：4

共 36 条

[1] Diastereoselective alkynylation of chiral non-racemic oxazolidines with mixed organoaluminum compounds [J].

Blanchet, J ;

Bonin, M ;

Chiaroni, A ;

Micouin, L ;

Riche, C ;

Husson, HP .

TETRAHEDRON LETTERS, 1999, 40 (15) :2935-2938

[2] Synthesis of enantiomerically pure α-substituted propargylic amines by reaction of organoaluminum reagents with oxazolidines [J].

Blanchet, J ;

Bonin, M ;

Micouin, L ;

Husson, HP .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) :6423-6426

[3] Catalytic enantioselective addition of dialkylzinc to N-diphenylphosphinoylimines.: A practical synthesis of α-chiral amines [J].

Boezio, AA ;

Charette, AB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (07) :1692-1693

[4] The asymmetric dialkylzinc addition to imines catalyzed by [2.2]paracyclophane-based N,O-ligands [J].

Dahmen, S ;

Bräse, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) :5940-5941

[5] Effect of ligand structure in the bisoxazoline mediated asymmetric addition of methyllithium to imines [J].

Denmark, SE ;

Stiff, CM .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (18) :5875-5878

[6] ENANTIOSELECTIVE SYNTHESIS OF ALLYL-AMINES, PROPARGYL-AMINES, AND 4-EN-2-YNYL-AMINES VIA 1,2-ADDITION OF ORGANOCERIUM REAGENTS TO CHIRAL ALDEHYDE IMINES [J].

ENDERS, D ;

SCHANKAT, J .

HELVETICA CHIMICA ACTA, 1995, 78 (04) :970-992

[7] Asymmetric synthesis of amines by nucleophilic 1,2-addition of organometallic reagents to the CN-double bond [J].

Enders, D ;

Reinhold, U .

TETRAHEDRON-ASYMMETRY, 1997, 8 (12) :1895-1946

[8]

Fässler R, 2002, ANGEW CHEM INT EDIT, V41, P3054, DOI 10.1002/1521-3773(20020816)41:16<3054::AID-ANIE3054>3.0.CO

[9]

2-B

[10]

FASSLER R, 2002, ANGEW CHEM, V114, P3180

← 1 2 3 4 →