Carreño M Carmen, Des Mazery Renaud, Urbano Antonio, Colobert Françoise, Solladié Guy
Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain.
Org Lett. 2004 Jan 22;6(2):297-9. doi: 10.1021/ol036299i.
[reaction: see text] The asymmetric synthesis of 2,7-cis-disubstituted oxepanes bearing a sulfoxide is achieved from commercially available precursors in only five steps. The key step is the highly diastereoselective Et3SiH/TMSOTf-promoted reductive cyclization of enantiopure hydroxysulfinyl aryl or alkyl ketones.