172689-07-5

Upstream product

• 67987-67-1 (4S)-4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolane 
• 98-59-9 p-toluenesulfonyl chloride 
• 165449-91-2 (2S,5R)-1,2-O-isopropylideneheptane-1,2,5-triol 

Relevant academic research and scientific papers

Functionalized Diorganozinc Compounds: Key Reagents for the Synthesis of Enantiomerically Pure 2,5-Disubstituted cis- and trans-Tetrahydrofurans

1,4-Diol derivatives 4a-i were synthesized stereoselectively by either reagent- or catalyst-controlled routes using the addition of functionalized diorganozinc reagents to aldehydes.The stereoselectivities along the reagent-controlled synthetic path were in the range between 80:20 and 95:5.The stereoselectivities along the catalyst route exceeded 95:5.The 1,4-diol derivatives 4 thus obtained were transformed into enantiomerically pure cis- and trans-2,5-disubstituted tetrahydrofurans (16-20) by means of an intramolecular Williamson reaction. - Keywords: Synthesis, stereoselective / Catalysis / Tetrahydrofurans / Dialkylzinc reagents