Collect. Czech. Chem. Commun. 2001, 66, 1521-1528

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


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.