Shi Epoxidation Diketal Catalyst

• CAT Number: R017000
• CAS Number: 18422-53-2
• Molecular Formula: C₁₂H₁₈O₆
• Molecular Weight: 258.27
• Purity: ≥95%
• Synonyms: 1,2:4,5-bis-O-(1-methylethylidene)-β-D-erythro-2,3-Hexodiulo-2,6-pyranose; Spiro[1,3-dioxolane-4,6’-[6H-1,3]dioxolo[4,5-c]pyran]-β-D-erythro-2,3-hexodiulo-2,6-pyranose deriv.; D-Epoxone; Epoxone; Shi catalyst
• Storage: -20°C
• IUPAC Name: (3'aR,4S,7'aR)-2,2,2',2'-tetramethylspiro[1,3-dioxolane-4,6'-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran]-7'-one
• InChI: InChI=1S/C12H18O6/c1-10(2)15-6-12(18-10)9(13)8-7(5-14-12)16-11(3,4)17-8/h7-8H,5-6H2,1-4H3/t7-,8-,12+/m1/s1
• InChIKey: IVWWFWFVSWOTLP-RWYTXXIDSA-N
• SMILES: CC1(OC[C@]2(O1)C(=O)[C@H]3[C@@H](CO2)OC(O3)(C)C)C

The Shi epoxidation diketal catalyst is an organocatalyst derived from fructose or related carbohydrates, featuring a chiral ketone with a cyclic diketal protecting group. It plays a pivotal role in asymmetric epoxidation, particularly of electron-deficient olefins, by forming dioxiranes in situ when reacted with oxone (potassium peroxymonosulfate). This chiral environment enables the selective formation of epoxides with high enantioselectivity. The diketal modification enhances the catalyst’s stability and solubility, making it effective under mild, aqueous conditions. It is widely applied in asymmetric synthesis for pharmaceutical and fine chemical development.