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

[11] Dihapto binding of aromatic molecules by π-basic transition metal complexes:: development of alternatives to the {Os(NH3)5}2+ fragment [J].

Brooks, BC ;

Gunnoe, TB ;

Harman, WD .

COORDINATION CHEMISTRY REVIEWS, 2000, 206 :3-61

[12] ON STEREOCHEMISTRY OF OSMIUM TETRAOXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EMPIRICAL RULE [J].

CHA, JK ;

CHRIST, WJ ;

KISHI, Y .

TETRAHEDRON, 1984, 40 (12) :2247-2255

[13] The synthesis of (-)-isodomoic acid C [J].

Clayden, J ;

Knowles, FE ;

Baldwin, IR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (08) :2412-2413

[14] Stereospecific dearomatising cyclisation of tertiary α-amidoorganolithiums [J].

Clayden, J ;

Knowles, FE ;

Menet, CJ .

SYNLETT, 2003, (11) :1701-1703

[15]

Clayden J, 2002, EUR J ORG CHEM, V2002, P3558

[16] Asymmetric deprotonation and dearomatising cyclisation of N-benzyl benzamides using chiral lithium amides:: formal synthesis of (-)-kainic acid [J].

Clayden, J ;

Menet, CJ ;

Mansfield, DJ .

CHEMICAL COMMUNICATIONS, 2002, (01) :38-39

[17]

CLAYDEN J, 2002, EUR J ORG CHEM, P2138

[18]

CLAYDEN J, 2004, TETRAHEDRON LETT, P1721

[19] Substituted diarylmethylamines by stereospecific intramolecular electrophilic arylation of lithiated ureas [J].

Clayden, Jonathan ;

Dufour, Jeremy ;

Grainger, Damian M. ;

Helliwell, Madeleine .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (24) :7488-+

[20] Synthesis of 2-oxazolines mediated by N,N′-diisopropylcarbodiimide [J].

Crosignani, S ;

Young, AC ;

Linclau, B .

TETRAHEDRON LETTERS, 2004, 45 (52) :9611-9615

← 1 2 3 4 5 →