Stereoselective dearomatizing addition of nucleophiles to uncomplexed benzene rings: A route to carbocyclic sugar analogues

被引：28

作者：

Clayden, Jonathan ^{[1
]}

Parris, Sean ^{[1
]}

Cabedo, Nuria ^{[1
]}

Payne, Andrew H. ^{[2
]}

机构：

[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

[2] GlaxoSmithKline, New Frontiers Sci Pk, Harlow CM19 8AY, Essex, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 27期

关键词：

carbohydrates; dearomatization; diastereoselectivity; oxazolines; pseudosugars;

D O I：

10.1002/anie.200801078

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Versatile synthetic intermediates were formed by the dearomatization of 2-aryl 4,5-diphenyloxazolines with secondary alkyl lithium reagents in the presence of N,N′-dimethylpropyleneurea (DMPU; see scheme). The resulting cyclohexadiene derivatives were converted into carbocyclic analogues of mannose and altrose in a short sequence without the use of protecting groups. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5060 / 5062

页数：3

共 42 条

[1] Caryose: A carbocyclic monosaccharide from Pseudomonas caryophylli [J].

Adinolfi, M ;

Corsaro, MM ;

DeCastro, C ;

Evidente, A ;

Lanzetta, R ;

Molinaro, A ;

Parrilli, M .

CARBOHYDRATE RESEARCH, 1996, 284 (01) :111-118

[2] Synthesis and conformational and biological aspects of carbasugars [J].

Arjona, Odon ;

Gomez, Ana M. ;

Cristobal Lopez, J. ;

Plumet, Joaquin .

CHEMICAL REVIEWS, 2007, 107 (05) :1919-2036

[3] Additions to functionalized arenes with concurrent dearomatization [J].

Bach, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (07) :729-730

[4]

Bach T., 1996, ANGEW CHEM, V108, P795

[5] Facile allylative dearomatization catalyzed by palladium [J].

Bao, M ;

Nakamura, H ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (04) :759-760

[6] Asymmetric conjugate nucleophilic addition of organolithiums to chromium (menthyloxy)(aryl)carbene complexes [J].

Barluenga, J ;

Trabanco, AA ;

Florez, J ;

GarciaGranda, S ;

Martin, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (51) :13099-13100

[7] ASYMMETRIC ADDITION TO CHIRAL NAPHTHYLOXAZOLINES - A FACILE ROUTE TO 1,1,2-TRISUBSTITUTED-1,2-DIHYDRONAPHTHALENES IN HIGH ENANTIOMERIC EXCESS [J].

BARNER, BA ;

MEYERS, AI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (06) :1865-1866

[8] Synthesis and biological activity of natural aminocyclopentitol glycosidase inhibitors: Mannostatins, trehazolin, allosamidins, and their analogues [J].

Berecibar, A ;

Grandjean, C ;

Siriwardena, A .

CHEMICAL REVIEWS, 1999, 99 (03) :779-844

[9]

Bernardinelli G, 2001, SYNTHESIS-STUTTGART, P2040

[10] Dearomatising cyclisation of lithiated l-naphthamides with a phenylglycinol-derived chiral auxiliary: asymmetric synthesis of an arylkainoid and a kainoid-like pyroglutamate [J].

Bragg, RA ;

Clayden, J ;

Bladon, M ;

Ichihara, O .

TETRAHEDRON LETTERS, 2001, 42 (20) :3411-3414

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