Simple 1,2-diamine ligands for asymmetric addition of aryllithium reagents to imines

被引：47

作者：

Cabello, N

Kizirian, JC

Gille, S

Alexakis, A

Bernardinelli, G

Pinchard, L

Caille, JC

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva, Switzerland

[2] PPG SIPSY, SI, F-49242 Avrille, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 22期

关键词：

diamines; asymmetric 1,2-addition; imines; organolithium compounds;

D O I：

10.1002/ejoc.200500447

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective addition of various aryllithium reagents to aromatic imines was catalyzed (20 mol-%) by readily accessible 1,2-diamines to afford a wide range of protected diarylmethylamines in up to 94% enantiomeric excess. Furthermore, the absolute configuration of these arylation products was determined by using X-ray crystallography. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).

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页码：4835 / 4842

页数：8

相关论文

共 61 条

[1] Chiral aminophosphine phosphinite ligands and related auxiliaries - Recent advances in their design, coordination chemistry, and use in enantioselective catalysis [J].

Agbossou-Niedercorn, F ;

Suisse, I .

COORDINATION CHEMISTRY REVIEWS, 2003, 242 (1-2) :145-158

[2] Three-component enantioselective synthesis of propargylamines through Zr-catalyzed additions of alkyl zinc reagents to alkynylimines [J].

Akullian, LC ;

Snapper, ML ;

Hoveyda, AH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (35) :4244-4247

[3] FURTHER-STUDIES OF THE KINETIC TEMPLATE EFFECT IN THE METAL ION-CATALYZED REACTIONS OF ORTHO-DONOR-SUBSTITUTED ARYL HALIDES WITH TERTIARY PHOSPHINES - STRUCTURAL REQUIREMENTS OF THE TEMPLATE [J].

ALLEN, DW ;

CROPPER, PE ;

SMITHURST, PG ;

ASHTON, PR ;

TAYLOR, BF .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (11) :1989-1994

[4] Enantioselective addition of organolithium reagents to imines mediated by C2-symmetric bis(aziridine) ligands [J].

Andersson, PG ;

Johansson, F ;

Tanner, D .

TETRAHEDRON, 1998, 54 (38) :11549-11566

[5] Synthesis of enantiomerically enriched amines by chiral ligand mediated addition of organolithium reagents to imines [J].

Arrasate, S ;

Lete, E ;

Sotomayor, N .

TETRAHEDRON-ASYMMETRY, 2001, 12 (14) :2077-2082

[6] AN EFFICIENT SYNTHESIS OF THE BENZHYDRYLPIPERAZINE DELTA-OPIOID AGONIST (+)-BW373U86 [J].

BISHOP, MJ ;

MCNUTT, RW .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (12) :1311-1314

[7] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].

Bloch, R .

CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438

[8] 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

[9] Transformation of (+)-thiomicamine into a new ligand for the enantioselective addition of methyllithium to prochiral imines [J].

Brózda, D ;

Chrzanowska, M ;

Gluszynska, A ;

Rozwadowska, MD .

TETRAHEDRON-ASYMMETRY, 1999, 10 (24) :4791-4796

[10] Enantioselective addition of aryllithium reagents to aromatic imines mediated by 1,2-diamine ligands [J].

Cabello, N ;

Kizirian, JC ;

Alexakis, A .

TETRAHEDRON LETTERS, 2004, 45 (24) :4639-4642

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