Synthesis of chiral functional polyhydroxylated arenes via Mukaiyama aldol reaction from Perlin aldehydes

• Published in: Carbohydrate research Vol. 535; p. 109004
• Main Authors: Halder, Suvendu, Moktan, Sangay, Sreeram, V, Kancharla, Pavan K
• Format: Journal Article
• Language: English
• Published: Netherlands 01-01-2024
• Subjects: Aldehydes; Ethers; Ethyl Ethers; Molecular Structure; Stereoisomerism; Silyl enol ethers; Glycal; Perlin aldehydes; Mukaiyama aldol reaction; Chiral aryl polyols
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2023.109004

Functionalized aryl polyhydroxylated compounds could be of great synthetic value for natural product synthesis. However, the synthesis of such compounds usually requires multi-step synthesis or the usage of sensitive reagents. We present here a practically simple route for the synthesis of such functionalized arylpolyols from glycal derived α,β-unsaturated 2,3-dideoxy aldehyde as well as α,β-saturated 2,3-dideoxy aldehyde (Perlin aldehydes) via Mukaiyama cross aldol condensation in the presence of silyl enol ether and TiCl
It was observed that the nature of the electronic substitution of the silyl enol ether does not play any role in the yield of the desired products. Further functionalization of the products has also been shown.