Double addition of grignard reagents to N-glycosyl nitrones:: A new tool for the contruction of enantiopure azaheterocycles

被引：32

作者：

Bonanni, M ^{[1
]}

Marradi, M ^{[1
]}

Cicchi, S ^{[1
]}

Faggi, C ^{[1
]}

Goti, A ^{[1
]}

机构：

[1] Univ Florence, CNR, ICCOM, Dipartimento Chim Organ Ugo Schiff, I-50019 Sesto Fiorentino, FI, Italy

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 02期

关键词：

D O I：

10.1021/ol047691e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

C-Pheynl-N-erythrosylnitrone 3 behaves as a C1,C1' bis-electrophile, undergoing a double addition of Grignard reagents in a domino fashion to afford acyclic hydroxylamines 4. The reaction proceeds at 0 degreesC with variable degrees of diastereoselectivity, from moderate to good. mainly depending on the organomagnesium reagent used. The usefulness of compounds 4 has been exemplified with the synthesis of pyrroloazepine 12 through a ring closing metathesis key step.

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页码：319 / 322

页数：4

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