Convenient synthesis of t-butyl Z-3-substituted glycidates under conditions of phase-transfer catalysis

✍ Scribed by Andrzej Jonczyk; Tomasz Zomerfeld

• Book ID: 104253148
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 90 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)00234-x

✦ Synopsis

Reactions of mixtures of t-butyl E-and Z-3-substituted glycidates 1a-h with 50% aq. sodium hydroxide and a catalyst, benzyltriethylammonium chloride, TEBAC in dichloromethane (phase-transfer catalysis, PTC) led to preferential hydrolysis of the E-isomers to afford pure (90-98%) t-butyl Z-3-substituted glycidates 1a-i in good yields; PTC cleavage of glycidates additionally substituted at C-2, 1g or C-3, 1h,i suggests that an aryl group in the Z isomers hampers attack of HO -on the carbonyl carbon atom. As described in the literature, the diastereoselective PTC synthesis of Z-3-substituted glycidates and glycidonitriles consists of fast hydrolysis of E isomers present in mixtures with Z ones.