Synthesis of an enantiomerically pure 2,2,4-trisubstituted cyclobutanone building block by zirconocene-promoted deoxygenative ring contraction of structurally modified 4-vinylfuranosides

被引：15

作者：

Paquette, LA ^{[1
]}

Kang, HJ

机构：

[1] Ohio State Univ, Evans Chem Labs, Columbus, OH 43210 USA

[2] Kyung Hee Univ, Dept Chem, Seoul 130701, South Korea

来源：

TETRAHEDRON | 2004年 / 60卷 / 06期

基金：

美国国家科学基金会;

关键词：

zirconocene; cyclobutanes; diastereoselectivity; D-glucose; ring contraction;

D O I：

10.1016/j.tet.2003.07.012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A route to an enantiopure trisubstituted cyclobutanone has been devised. The pursuit of this building block begins With D-glucose and features a zirconocene-promoted ring contraction. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：1353 / 1358

页数：6

共 15 条

[1]

Boeckman R.K., 2000, J ORG SYN, V77, P141, DOI 10.15227/orgsyn.077.0141

[2]

HANZAWA Y, 1995, SYNLETT, P299

[3]

HASE T, 1995, ENCY REAGENTS ORGANI, V7, P4533

[4] REACTIONS OF HYDROXYL-GROUPS WITH "TOSYLCHLORIDE-DIMETHYLAMINOPYRIDINE SYSTEM - DIRECT SYNTHESIS OF CHLORIDES FROM HYDROXYCOMPOUNDS [J].

HWANG, CK ;

LI, WS ;

NICOLAOU, KC .

TETRAHEDRON LETTERS, 1984, 25 (22) :2295-2296

[5] ZIRCONIUM-MEDIATED, HIGHLY DIASTEREOSELECTIVE RING CONTRACTION OF CARBOHYDRATE-DERIVATIVES - SYNTHESIS OF HIGHLY FUNCTIONALIZED, ENANTIOMERICALLY PURE CARBOCYCLES [J].

ITO, H ;

MOTOKI, Y ;

TAGUCHI, T ;

HANZAWA, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (19) :8835-8836

[6] OXIDATION-PRODUCTS OF ARACHIDONIC-ACID .3. THE SYNTHESIS OF METHYL 8R,9R,11R, 8S,9R,11R, AND 8S,9S,11R-TRIACETOXYEICOSA-5Z,12E,14Z-TRIENOATE [J].

JUST, G ;

LUTHE, C .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1980, 58 (21) :2286-2294

[7] METAL-PROMOTED CYCLIZATION .11. REACTION OF ZIRCONOCENE DICHLORIDE WITH ALKYLLITHIUMS OR ALKYL GRIGNARD-REAGENTS AS A CONVENIENT METHOD FOR GENERATING A ZIRCONOCENE EQUIVALANT AND ITS USE IN ZIRCONIUM-PROMOTED CYCLIZATION OF ALKENES, ALKYNES, DIENES, ENYNES, AND DIYNES [J].

NEGISHI, E ;

CEDERBAUM, FE ;

TAKAHASHI, T .

TETRAHEDRON LETTERS, 1986, 27 (25) :2829-2832

[8] ALLYLIC AND PROPARGYLIC IMIDIC ESTERS IN ORGANIC-SYNTHESIS [J].

OVERMAN, LE .

ACCOUNTS OF CHEMICAL RESEARCH, 1980, 13 (07) :218-224

[9]

Paquette LA, 2002, SYNTHESIS-STUTTGART, P2105

[10] Diastereoselectivity control in the zirconocene-mediated ring contraction of 4-vinylfuranosides to enantiopure multiply functionalized cyclobutanes [J].

Paquette, LA ;

Cunière, N .

ORGANIC LETTERS, 2002, 4 (11) :1927-1929

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