Bicyclo[3.1.0]hexanes from sugar-derived diazo compounds and iodonium ylides. Diastereocontrol and synthetic applications

被引：18

作者：

Gallos, JK ^{[1
]}

Koftis, TV ^{[1
]}

Massen, ZS ^{[1
]}

Dellios, CC ^{[1
]}

Mourtzinos, IT ^{[1
]}

Coutouli-Argyropoulou, E ^{[1
]}

Koumbis, AE ^{[1
]}

机构：

[1] Aristotle Univ Thessaloniki, Dept Chem, GR-54006 Thessaloniki, Greece

来源：

TETRAHEDRON | 2002年 / 58卷 / 40期

关键词：

diazo compounds; iodonium ylides; cyclopropanation; nucleosides; carbohydrates; copper(I) iodide; rhodium(II) acetate;

D O I：

10.1016/S0040-4020(02)01002-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Cut and Rh-2(OAc)(4) catalyzed decomposition of ethyl 2-diazo-4,5-isopropylidenedioxy-3-oxo-6-heptenoate results in intramolecular cyclopropanation products with opposite diastcreoselectivity. In contrast, decomposition of the respective iodonium ylide can proceed without catalysts to give the cyclopropanation products with diastereoselectivity unchangeable by the presence of Cut and Rh-2(OAc)(4), revealing thus, that in this particular case the reaction is an electrophilic addition of the iodonium center to the double bond. The synthetic importance of these reactions has been demonstrated by preparing a number of precursors of cyclopentyl, cyclopropyl and bicyclo[3,1,0]hexyl antiviral carbocyclic nucleosides. (C) 2002 Elsevier Science Ltd. All lights reserved.

引用

页码：8043 / 8053

页数：11

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