ChemInform Abstract: Enantioselective Reactions of α‐Methoxybenzyllithium Generated by t‐BuLi/Chiral Bis(oxazoline) Complex with Aldehydes.

Abstract

1999 stereochemistry stereochemistry (general, optical resolution) O 0030 -050Enantioselective Reactions of α-Methoxybenzyllithium Generated by t-BuLi/Chiral Bis(oxazoline) Complex with Aldehydes. -The title reaction gives access to 1,2-diol monomethyl ethers (III) in moderate to high levels of enantioselectivity (up to 98%) and diastereoselectivity (up to 90% anti), depending on the aldehyde reactivity. The present reaction provides a new way for the asymmetric synthesis of propargylic alcohols such as (IIIc) and (IIId). The origin of the enantioselectivity is discussed in terms of a dynamic thermodynamic resolution mechanism. -(TOMOOKA,