Isohexides as Versatile Scaffolds for Asymmetric Catalysis

被引：16

作者：

Kadraoui, Mohammed ^{[1
,2
,3
]}

Maunoury, Thibault ^{[1
,2
]}

Derriche, Zoubir ^{[3
]}

Guillarme, Stephane ^{[1
,2
]}

Saluzzo, Christine ^{[1
,2
]}

机构：

[1] CNRS, UMR 6283, IMMM, F-72085 Le Mans, France

[2] Univ Maine, F-72085 Le Mans, France

[3] Univ Sci & Technol, Dept Genie Mat, LPCMCE, Mohamed Boudiaf 31000, El Mnouar Oran, Algeria

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 03期

关键词：

Organocatalysis; Asymmetric catalysis; Carbohydrates; Isomannide; Isosorbide; TETRAHYDROFURAN BUILDING-BLOCKS; DIELS-ALDER REACTIONS; CHIRAL LIGANDS; ISOMANNIDE; HYDROGENATION; ISOSORBIDE; COMPLEXES; ALCOHOLS; MICHAEL; KETONES;

D O I：

10.1002/ejoc.201402851

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This review presents an overview of the use of dianhydrohexitol derivatives as asymmetric ligands in organometallic catalysis or as asymmetric organocatalysts. For that purpose, we highlight two series of derivatives, the first preserving the original bisfused THF backbones, and the second originating from single THF ring-opening reactions. These derivatives have been involved in different asymmetric reactions for the formation of C-H, C-C, C-N, or C-S bonds.

引用

页码：441 / 457

页数：17

共 67 条

[1] 1,4-3,6-DIANHYDRO-2,5-DIDEOXY-2,5-BIS(DIPHENYLPHOSPHINO)-L-IDITOL - A NEW CHIRAL LIGAND FOR ASYMMETRIC HYDROGENATION WITH RHODIUM COMPLEXES AS CATALYSTS [J].

BAKOS, J ;

HEIL, B ;

MARKO, L .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 253 (02) :249-252

[2] Sugar alcohols XXI A study of the effect of the anhydrides of sorbitol on the dissociation constant of boric acid [J].

Bell, FK ;

Carr, CJ ;

Krantz, JC .

JOURNAL OF PHYSICAL CHEMISTRY, 1940, 44 (07) :862-865

[3]

Blackmond DG, 1999, ANGEW CHEM INT EDIT, V38, P2196, DOI 10.1002/(SICI)1521-3773(19990802)38:15<2196::AID-ANIE2196>3.0.CO

[4]

2-9

[5]

BLACKMOND DG, 1999, ANGEW CHEM, V111, P2333

[6] New modular P-chiral ligands for Rh-catalyzed asymmetric hydrogenation [J].

Bondarev, Oleg G. ;

Goddard, Richard .

TETRAHEDRON LETTERS, 2006, 47 (51) :9013-9015

[7] Technology development for the production of biobased products from biorefinery carbohydrates-the US Department of Energy's "Top 10" revisited [J].

Bozell, Joseph J. ;

Petersen, Gene R. .

GREEN CHEMISTRY, 2010, 12 (04) :539-554

[8] A concise synthesis of a rigid isomannide-based diphosphine ligand and structural characterisation of an alkoxyphosphonium intermediate [J].

Carcedo, C ;

Dervisi, A ;

Fallis, IA ;

Ooi, L ;

Malik, KMA .

CHEMICAL COMMUNICATIONS, 2004, (10) :1236-1237

[9] DIHYDROFURAN AND TETRAHYDROFURAN BUILDING-BLOCKS FROM 1,4/3,6-DIANHYDROMANNITOL .1. SYNTHESIS OF (1S,5R,7R)-ENDO-(-)-BREVICOMIN AND (1S,5R,7S)-(-)-EXO-BREVICOMIN AND (R)-(+)-DODECANOLIDE [J].

CERE, V ;

MAZZINI, C ;

PAOLUCCI, C ;

POLLICINO, S ;

FAVA, A .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) :4567-4571

[10] ALKYLLITHIUM-PROMOTED RING FISSIONS OF HALIDES DERIVED FROM 1,4-3,6-DIANHYDROHEXITOLS [J].

CERE, V ;

PAOLUCCI, C ;

POLLICINO, S .

TETRAHEDRON LETTERS, 1989, 30 (48) :6737-6740

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