Enantioselective reactions of α-methoxybenzyllithium generated by t-BuLi/chiral bis(oxazoline) complex with aldehydes

✍ Scribed by Katsuhiko Tomooka; Lan-Fang Wang; Nobuyuki Komine; Takeshi Nakai

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 239 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)01365-9

✦ Synopsis

The title reaction is shown to afford the corresponding 1,2-diol monomethyl ethers in moderate-to-high levels of % ee (up to 98%) and % de (up to 90% anti), depending markedly on the aldehyde reactivity. The origin of the enantioselectivity is discussed in terms of a dynamic thermodynamic resolution mechanism.