An Entry to 1,7-Dioxaspiro[5.6]dodecanes and 1,6-Dioxaspiro[4.6]undecanes

Anthony Ollivier (1) , M.-E. Sinibaldi (1) , Loïc Toupet (2) , Mounir Traïkia (1) , Isabelle Canet (1)

1 SEESIB - Synthèse et étude de systèmes à intêret biologique
2 GMCM - Groupe matière condensée et matériaux

Ketones 11a–c obtained by iterative alkylation of acetone N,N-dimethylhydrazone with iodides 6 and 8a,b or epoxide 9 followed by SiO2/H2O-induced cleavage of the hydrazone were quantitatively transformed into 1,6-dioxaspiro[4.6]undecanes 12a,c and 1,7-dioxaspiro[5.6]dodecanes 12b using Yb(OTf)3 in CH3CN.

Mots clés: Alkylation; Cyclization; Hydrazone; Spiroketal

Domaines: Physique [physics]

Anthony Ollivier, M.-E. Sinibaldi, Loïc Toupet, Mounir Traïkia, Isabelle Canet. An Entry to 1,7-Dioxaspiro[5.6]dodecanes and 1,6-Dioxaspiro[4.6]undecanes. Tetrahedron Letters, 2010, 51, pp.4147-4149. ⟨10.1016/j.tetlet.2010.06.003⟩. ⟨hal-00506245⟩