196618-85-6Relevant articles and documents
Asymmetrization of a meso 1,2-enediol bis(trimethylsilyl) ether using a (S)-BINOL monoisopropyl ether(BINOL-Pr(i))-tin tetrachloride complex: An alternative route to (-)-ketodicyclopentadiene and (-)-ketotricyclononene
Taniguchi, Takahiko,Ogasawara, Kunio
, p. 6429 - 6432 (1997)
A tricyclic mesa 12-enediol bis(trimethylsilyl) ether having an endo-tricyclo[4.2.1.02,5]nonene framework has been asymmetrically desymmetrized by protonation with a complex generated from (S)-BINOL monoisopropyl ether (BINOL-Pr(i)) and tin tetrachloride to give the optically enriched acyloin in 90% ee. The chiral acyloin thus obtained has been transformed into two versatile chiral building blocks, (-)-ketodicyclopentadiene and (-)-ketotricyclononene, in optically pure forms via a sequence involving concurrent enzymatic acetylation and optical purification.
Lipase-triethylamine-mediated dynamic transesterification of a tricyclic acyloin having a latent meso-structure: A new route to optically pure oxodicyclopentadiene
Taniguchi, Takahiko,Ogasawara, Kunio
, p. 1399 - 1400 (1997)
The racemic tricyclic acyloin (±)-endo-3-hydroxytricyclo[4.2.1.02,5]non-7-en-4-one has been dynamically resolved via the transient formation of the meso-enediol isomer under lipase-triethylamine-mediated kinetic transesterification conditions to give the single chiral acetate (-)-endo-3-acetoxytricyclo[4.2.1.02,5]non-7-en-4-one, serving as a precursor of (-)-oxodicyclopentadiene, in excellent optical and chemical yields.
