Diastereoselective alkylation of (arene)tricarbonylchromium and ferrocene complexes using a chiral, C2-symmetrical 1,2-diamine as auxiliary

被引：24

作者：

Alexakis, A ^{[1
]}

Tomassini, A ^{[1
]}

Andrey, O ^{[1
]}

Bernardinelli, G ^{[1
]}

机构：

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

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 07期

关键词：

animals; chromium; diamines; homogeneous catalysis; planar chirality;

D O I：

10.1002/ejoc.200400662

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The aminal of (benzaldehyde)tricarbonylchromium and enantiopure bipyrrolidine undergoes diastereoselective orthometallation with butyllithium. Quenching with various electrophiles, followed by hydrolysis of the aminal, affords orthosubstituted (benzaldehyde)tricarbonylchromium compounds with high ee (91-99 %). When quenched with Ph2PCl, a new chiral PN-bidentate ligand is obtained, which shows effi- ciency in Pd- and Cu-catalysed reactions. The aminal of ferrocenecarbaldehyde could also be formed, but the ortho-deprotonation occurs with only moderate diastereoselectivity (70%).(c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).

引用

页码：1332 / 1339

页数：8

共 76 条

[1] ENANTIOSELECTIVE ORTHO-LITHIATION OF BENZALDEHYDE CHROMIUMTRICARBONYL COMPLEX [J].

ALEXAKIS, A ;

KANGER, T ;

MANGENEY, P ;

ROSEMUNCH, F ;

PERROTEY, A ;

ROSE, E .

TETRAHEDRON-ASYMMETRY, 1995, 6 (09) :2135-2138

[2] ENANTIOSELECTIVE ORTHO-LITHIATION OF AMINALS OF BENZALDEHYDE CHROMIUMTRICARBONYL COMPLEX [J].

ALEXAKIS, A ;

KANGER, T ;

MANGENEY, P ;

ROSEMUNCH, F ;

PERROTEY, A ;

ROSE, E .

TETRAHEDRON-ASYMMETRY, 1995, 6 (01) :47-50

[3] Dramatic improvement of the enantiomeric excess in the asymmetric conjugate addition reaction using new experimental conditions [J].

Alexakis, A ;

Benhaim, C ;

Rosse, S ;

Humam, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (19) :5262-5263

[4] RESOLUTION AND ASYMMETRIC-SYNTHESIS OF ORTHO-SUBSTITUTED (BENZALDEHYDE)TRICARBONYLCHROMIUM COMPLEXES [J].

ALEXAKIS, A ;

MANGENEY, P ;

MAREK, I ;

ROSEMUNCH, F ;

ROSE, E ;

SEMRA, A ;

ROBERT, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) :8288-8290

[5]

Alexakis A, 2000, ANGEW CHEM INT EDIT, V39, P4093, DOI 10.1002/1521-3773(20001117)39:22<4093::AID-ANIE4093>3.0.CO

[6]

2-R

[7]

Alexakis A, 2002, EUR J ORG CHEM, V2002, P3221

[8]

ALEXAKIS A, 1998, ORG SYNTH, V76, P23

[9]

[Anonymous], 1995, Comprehensive Organometallic Chemistry II

[10] ASYMMETRIC DEPROTONATION AND COMPLEXATION REACTIONS MEDIATED BY CHIRAL KETALS AS A ROUTE TO ORTHO-DISUBSTITUTED (ETA-6-ARENE)CR(CO)3 COMPLEXES [J].

AUBE, J ;

HEPPERT, JA ;

MILLIGAN, ML ;

SMITH, MJ ;

ZENK, P .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) :3563-3570

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