Double addition of grignard reagents to N-glycosyl nitrones: a new tool for the construction of enantiopure azaheterocycles.
[Reaction: see text] C-Phenyl-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 degrees C 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.
Bonanni
Marco
M
Dipartimento di Chimica Organica Ugo Schiff, Università di Firenze, ICCOM, C.N.R., via della Lastruccia 13, I-50019 Sesto Fiorentino (FI), Italy.
Marradi
Marco
M
Cicchi
Stefano
S
Faggi
Cristina
C
Goti
Andrea
A
D000838:Anions; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D006031:Glycosylation; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008274:Magnesium / Q000737:chemistry*; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism
D000838:Anions; D001372:Aza Compounds; D006571:Heterocyclic Compounds; D009589:Nitrogen Oxides; D009942:Organometallic Compounds; C015388:nitrones; D002244:Carbon; D008274:Magnesium