C1-symmetric sulfoximines as ligands in copper-catalyzed asymmetric Mukaiyama-type aldol reactions

被引：157

作者：

Langner, M ^{[1
]}

Bolm, C ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 44期

关键词：

aldol reaction; asymmetric catalysis; copper; N ligands; sulfoximines;

D O I：

10.1002/anie.200460953

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Aldol products with quarternary centers have been obtained with up to 99% ee in high yields by using copper(II) catalysts bearing C1-symmetric aminosulfoximines as ligands (see scheme). In terms of ee values and yield the new catalysts compare well with established systems based on metal complexes with bis(oxazoline) and pyridylbis(oxazoline) ligands.

引用

页码：5984 / 5987

页数：4

共 52 条

[1]

Anderson ME, 1998, CHEM-BIOL INTERACT, V112, P1

[2] The stability of pseudopeptides bearing sulfoximines as chiral backbone modifying element towards proteinase K [J].

Bolm, C ;

Müller, D ;

Dalhoff, C ;

Hackenberger, CPR ;

Weinhold, E .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (19) :3207-3211

[3] C2-symmetric bissulfoximines as ligands in copper-catalyzed enantioselective Diels-Alder reactions [J].

Bolm, C ;

Martin, M ;

Simic, O ;

Verrucci, M .

ORGANIC LETTERS, 2003, 5 (04) :427-429

[4] Spectroscopic investigations of bis(sulfoximine) copper(II) complexes and their relevance in asymmetric catalysis [J].

Bolm, C ;

Martin, M ;

Gescheidt, G ;

Palivan, C ;

Neshchadin, D ;

Bertagnolli, H ;

Feth, M ;

Schweiger, A ;

Mitrikas, G ;

Harmer, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (20) :6222-6227

[5] A new class of C1-symmetric monosulfoximine ligands for enantioselective hetero Diels-Alder reactions [J].

Bolm, C ;

Verrucci, M ;

Simic, O ;

Cozzi, PG ;

Raabe, G ;

Okamura, H .

CHEMICAL COMMUNICATIONS, 2003, (22) :2826-2827

[6] Turn formation initiated by a bissulfoximine motif: Synthesis and structural investigation [J].

Bolm, C ;

Muller, D ;

Hackenberger, PR .

ORGANIC LETTERS, 2002, 4 (06) :893-896

[7]

Bolm C, 2001, SYNLETT, P1878

[8]

Bolm C, 2001, CHEM-EUR J, V7, P1118, DOI 10.1002/1521-3765(20010302)7:5<1118::AID-CHEM1118>3.0.CO

[9]

2-3

[10]

Bolm C, 2000, SYNTHESIS-STUTTGART, P911

← 1 2 3 4 5 6 →