SmI2-mediated 3-exo-trig cyclization of β,γ-unsaturated carbonyl compounds: diastereoselective synthesis of cyclopropanols.
SmI(2)-mediated 3-exo-trig cyclizations of β,γ-unsaturated carbonyl compounds to generate cyclopropanols are not generally observed processes. The reported examples are limited to β,γ-unsaturated carbonyl compounds that possess ester groups conjugated with the alkene unit. The results of the current study show that this cyclization also occurs when other substitution patterns are present on the alkene moiety, affording (E)-cyclopropanols in good to excellent yields and in most cases with high degrees of diastereoselectivity.
Martin-Fontecha
Mar
M
Departamento de Quimica Organica I, Facultad de Ciencias Quimicas, Universidad Complutense, 28040 Madrid, Spain.
Agarrabeitia
Antonia R
AR
Ortiz
Maria J
MJ
Armesto
Diego
D