Collect. Czech. Chem. Commun.
2001, 66, 1521-1528
https://doi.org/10.1135/cccc20011521
Spiro[4.5]deca-2,7-diene-1,6-dione and Spiro[5.5]undeca-2,8-diene-1,7-dione. Synthesis, Reductions and Palladium-Catalyzed Allylic Substitutions
Doina Sirbu* and Valeriu Sunel
Department of Organic Chemistry, "Al. I. Cuza" University of Iasi, Bd. Carol I, 11, 6600 Iasi, Romania
Abstract
Spiro[4,5]deca-2,7-diene-1,6-dione (2a) and spiro[5,5]undeca-2,8-diene-1,7-dione (2b) were prepared by a direct synthesis starting from diethyl malonate. The two-step 1,2-reductions (NaBH4/CeCl3) of the diones gave cis/trans-diols, which could be easily transformed into diacetates. Both diacetates were subjected to Pd(0)-catalyzed allylic alkylations, in which the relative stereochemistry was retained.
Keywords: Spirodecane; Spiroundecane; Spirocyclic compounds; Spiranes; Reductions; Allylic substitutions; Cyclic allyl alcohols.
References: 14 live references.
