𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Unusual cycloaddition of an unsaturated nitrone to a vinylogous ester

✍ Scribed by L.R. Heppt; J. Bordner; T.A. Bryson

Book ID
104222348
Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
180 KB
Volume
26
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

The anomalous addition of a-dichloro-N-cyclohexylpropanaldonitrone (1) to the carbonyl of quinoidal, vinylogous ester 2 is reported.

Chemical investigations of nitrones and unsaturated

nitronesl has led to important synthetic

πŸ“œ SIMILAR VOLUMES

1,3-Dipolar cycloadditions of cyclic nit
1,3-Dipolar cycloadditions of cyclic nitrones to Ξ³-bromo Ξ±,Ξ²-unsaturated esters and lactones
✍ Pedro de March; Marta Figueredo; Josep Font; Antonio Salgado πŸ“‚ Article πŸ“… 1998 πŸ› Elsevier Science 🌐 French βš– 630 KB

The 1,3-dipolar cycloaddition of cyclic nitrones to several "t-bromo ct,~unsaturated esters and lactones has been studied. All the reactions have shown high stereoselectivity, with a predominance of the endo or exo transition state for the trans or cis dipolarophiles, respectively.

[1,3]-Dipolar intramolecular nitrone ole
[1,3]-Dipolar intramolecular nitrone olefin cycloaddition reaction of a sugar-derived Ξ±,Ξ²-unsaturated ester: a new diastereo- and regioselective synthesis of an aminocyclopentitol
✍ Santosh M Jachak; Navnath P Karche; Dilip D Dhavale πŸ“‚ Article πŸ“… 2001 πŸ› Elsevier Science 🌐 French βš– 92 KB

The reaction of hemiacetal 2a, from the sugar derived a,b-unsaturated ester 1a, with N-benzylhydroxylamine hydrochloride in situ generates an N-benzylnitrone as a 1,3-dipole, which spontaneously undergoes diastereo-and regioselective intramolecular nitrone olefin cycloaddition to afford a hydroxy fu