Asymmetric Mukaiyama aldol reaction of a ketene silyl acetal of thioester catalyzed by a binaphthol–titanium complex in supercritical fluoroform

✍ Scribed by Koichi Mikami; Satoru Matsukawa; Yoshihito Kayaki; Takao Ikariya *

• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 109 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)00063-0

✦ Synopsis

The Mukaiyama aldol reaction catalyzed by a binaphthol-derived chiral titanium(IV) complex proceeds smoothly in an unorthodox reaction medium, supercritical fluid (SCF) such as fluoroform (scCHF 3 ). The chemical yield and enantioselectivity of the reaction in SCFs are found to be tuned by changing the supercritical fluids, scCHF 3 versus carbon dioxide (scCO 2 ), and adjusting the matched polarities by varying the pressure of CHF 3 .