Asymmetric addition of 2-methylfuran and its lithiated derivative to variously N,N-protected l-alaninals

Metalated Heterocycles and Their Applications in Synthetic Organic Chemistry

“…Thus, 2-lithiofurans prepared by direct deprotonation have been used in the last several years in alkylation reactions for the synthesis of (+)-patulolide, (−)-pyrenophorin, (+)-aspicilin,30b and arachidonic or linoleic esters of 2-lysophosphatidylcholine . In addition, they have been employed in addition reactions to aldehydes in alaninals, to benzaldehyde for the synthesis of oxyporphyrin building blocks using 2,5-dilithiated furans, and to dialdoses and other aldehydes for the synthesis of some natural products . Different ketones have been used as electrophiles, such as cyclobutenones, the glucofuranoulose 9 for the preparation of pyranosides 12 [after reaction with 10 and oxidative ring opening of the furan ring in derivative 11 with N - bromosuccinimide (NBS) and final methylation] (Scheme ) and in the synthesis of polyquinane ring systems, diterpene skeletons, or diarylanthrones …”

Short and Efficient Synthesis of Chiral Furyl Carbinols from Carbohydrates

“…To prepare chiral furyl carbinols, several methods have been developed, including asymmetric reduction of furyl ketones, acid- or base-promoted addition of furan to chiral aldehydes, aldol reaction of chiral enolates with furfurals, Sharpless dihydroxylation of vinyl furans, and resolution of racemic mixtures 2 …”