Photoinduced metalation of nonactivated C-Cl bonds with samarium diiodide: synthesis of alkenes with high (Z)-selectivity through beta-elimination reactions.
[reaction: see text] The photoinduced metalation of nonactivated C-Cl bonds of O-acetyl chlorohydrins is promoted by samarium diiodide. As a result of this, beta-elimination of O-acetyl chlorohydrins is achieved, affording the corresponding (Z)-alkenes with total or high stereoselectivity.
Concellón
José M
JM
Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, C/Julián Clavería, 8, 33006, Oviedo, Spain. jmcg@fq.uniovi.es
Rodríguez-Solla
Humberto
H
Simal
Carmen
C
Huerta
Mónica
M