Second-generation N,O-[2.2]paracyclophane ketimine ligands for the alkenylzinc addition to aliphatic and aromatic aldehydes:: Scope and limitations

被引：38

作者：

Lauterwasser, Frank ^{[1
]}

Gall, Julia ^{[1
]}

Hoefener, Sebastian ^{[1
]}

Braese, Stefan ^{[1
]}

机构：

[1] Univ Karlsruhe TH, Inst Organ Chem, D-76131 Karlsruhe, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2006年 / 348卷 / 15期

关键词：

alkenylzinc reagents; asymmetric catalysis; chiral allylic alcohols; N; O ligands; paracyclophanes;

D O I：

10.1002/adsc.200606193

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Second generation N,O-[2.2]paracy-clophane ketimine ligands were investigated for their ability to catalyze the 1,2-addition of alkenylzinc reagents to aliphatic and aromatic aldehydes with special focus on functionalized substrates. For aliphatic aldehydes, which have always been challenging in this field, remarkably high enantiomeric excesses could be determined (50-95 % ee). However, alkenylzinc reagents bearing heteroatoms proved to be demanding substrates for this system.

引用

页码：2068 / 2074

页数：7

共 70 条

[41] CATALYTIC ASYMMETRIC-SYNTHESIS OF SECONDARY (E)-ALLYL ALCOHOLS FROM ACETYLENES AND ALDEHYDES VIA (1-ALKENYL)ZINC INTERMEDIATES - PRELIMINARY COMMUNICATION [J].

OPPOLZER, W ;

RADINOV, RN .

HELVETICA CHIMICA ACTA, 1992, 75 (01) :170-173

[42] Catalytic asymmetric synthesis of macrocyclic (E)-allylic alcohols from ω-alkynals via intramolecular 1-alkenylzinc/aldehyde additions [J].

Oppolzer, W ;

Radinov, RN ;

El-Sayed, E .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (14) :4766-4770

[43] ENANTIOSELECTIVE SYNTHESIS OF SEC-ALLYLALCOHOLS BY CATALYTIC ASYMMETRIC ADDITION OF DIVINYLZINC TO ALDEHYDES [J].

OPPOLZER, W ;

RADINOV, RN .

TETRAHEDRON LETTERS, 1988, 29 (44) :5645-5648

[44] Synthesis of planar chiral [2.2]paracyclophanes by biotransformations: Kinetic resolution of 4-formyl-[2.2]paracyclophane by asymmetric reduction [J].

Pamperin, D ;

Hopf, H ;

Syldatk, C ;

Pietzsch, M .

TETRAHEDRON-ASYMMETRY, 1997, 8 (02) :319-325

[45] Asymmetric alkynylzinc additions to aldehydes and ketones [J].

Pu, L .

TETRAHEDRON, 2003, 59 (50) :9873-9886

[46] Catalytic asymmetric organozinc additions to carbonyl compounds [J].

Pu, L ;

Yu, HB .

CHEMICAL REVIEWS, 2001, 101 (03) :757-824

[47] Enantioselective addition of vinylzinc reagents to aldehydes catalyzed by modular ligands derived from amino acids [J].

Richmond, ML ;

Sprout, CM ;

Seto, CT .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (22) :8835-8840

[48] Efficient synthesis of enantiomerically and diastereomerically pure [2.2]paracyclophane-based N,O-ligands [J].

Rozenberg, VI ;

Danilova, TI ;

Sergeeva, EV ;

Shouklov, IA ;

Starikova, ZA ;

Hopf, H ;

Kühlein, K .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (03) :432-440

[49] Enantiomerically pure (R)- and (S)-15-Hydroxy[2.2]paracyclophane-4-carbaldehyde (iso-FHPC):: A novel parent compound for planar chiral ligands [J].

Rozenberg, VI ;

Antonov, DY ;

Sergeeva, EV ;

Vorontsov, EV ;

Starikova, ZA ;

Fedyanin, IV ;

Schulz, C ;

Hopf, H .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (11) :2056-2061

[50] Phenyl versus ethyl transfer in the addition of organozinc reagents to aldehydes: A theoretical study [J].

Rudolph, J ;

Rasmussen, T ;

Bolm, C ;

Norrby, PO .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (26) :3002-3005

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