Abstract
A trans‐selective access to enol ethers with a disubstituted C=C bond was developed. It consists of a diastereoselective glycolate aldol addition, a hydrolysis, and a Grob fragmentation. Aldol additions of N‐[(benzyloxy)acetyl]oxazolidinones furnished syn‐aldols selectively. Hydrolytic removal of the auxiliaries gave α‐benzyloxy‐β‐hydroxycarboxylic acids. Exposure to DMF dineopentylacetal induced Grob fragmentations, which delivered trans‐configured enol ethers. Applying our 3‐step sequence in a bidirectional synthesis led to bis(enol ethers) trans,trans‐selectively, i.e., to a motif rarely encountered in the literature. A modified precursor synthesis allowed for the first time to access both the E‐ and the Z‐isomer of an enol ether with a trisubstituted C=C bond stereoselectively using a Grob fragmentation route. The Ar–Br and C≡C–SiMe2tBu motifs of appropriate enol ethers engaged in follow‐up reactions via organometallics. These provided more elaborated enol ethers.
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