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

Double Addition of Grignard Reagents to N-Glycosyl Nitrones: a New Tool for the Construction of Enantiopure Azaheterocycles / M. BONANNI; M. MARRADI; S. CICCHI; C. FAGGI; A. GOTI. - In: ORGANIC LETTERS. - ISSN 1523-7060. - STAMPA. - 7:(2005), pp. 319-322.

Double Addition of Grignard Reagents to N-Glycosyl Nitrones: a New Tool for the Construction of Enantiopure Azaheterocycles

BONANNI, MARCO;M. MARRADI;CICCHI, STEFANO;FAGGI, CRISTINA;GOTI, ANDREA
2005

Abstract

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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319
322
M. BONANNI; M. MARRADI; S. CICCHI; C. FAGGI; A. GOTI
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2158/334337
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