An entry to 1,6-dioxaspiro[4.6]undecanes and 1,7-dioxaspiro[5.6]dodecanes
✍ Scribed by Anthony Ollivier; Marie-Eve Sinibaldi; Loïc Toupet; Mounir Traïkia; Isabelle Canet
- Book ID
- 104097927
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- French
- Weight
- 591 KB
- Volume
- 51
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
Ketones 11a-c obtained by iterative alkylation of acetone N,N-dimethylhydrazone with iodides 6 and 8a,b or epoxide 9 followed by SiO 2 /H 2 O-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 CH 3 CN.
📜 SIMILAR VOLUMES
Acid-catalyzed equilibration of spiroketals 5SHp6 and 55Haj3 involves a two stage process whereby the 1,6-dioxaspiro]4.4]nonanes can be equilibrated under mild conditions to a pair of 1,6\_dioxaspiro[45]decanes with preservation of the adjacent C-20 methyl stereocenter. Under more forcing conditions