Homochiral cis, cis-; cis,trans- and trans, trans-spiro[4.4]nonane-1,6
-diols were prepared via diastereoselective reduction of enantiomerica
lly pure spiro[4.4]nonane-1,6-dione (1) with the corresponding reducin
g agents: lithium n-butyldiisobutylaluminium hydride for cis,cis-diol
(2) with 88% yield; BH3. HF for cis,trans-diol (3) with 91% yield; LiA
lH4 for trans,trans-diol (4) with 15% yield.