194654-38-1

Upstream product

• 100572-69-8 (2R,3S,4S)-3-Bnzyloxy-1,2-O-isopropylidene-4-methyl-5-hexene-1,2-diol 
• 194654-37-0 (R)-4-((1S,2S)-1-Benzyloxy-2-methyl-but-3-ynyl)-2,2-dimethyl-[1,3]dioxolane 

Downstream Products

• 194654-39-2 C₁₇H₂₁⁽²⁾H₂⁽³⁾HO₃ 

Relevant academic research and scientific papers

A mechanistically unusual base induced [1,3]-H-shift in homoallylic ethers

Upon treatment with NaH in DMF the homoallylic ethers 1a-g and the amine 1h undergo a rearrangement into the trisubstituted (E)-olefins 2a-h. Experiments with isotopically labelled forms of 1a and 1b show that the [1,3]-shift is cleanly intramolecular and proceeds predominantly in the suprafacial mode.