Lipase TL®-mediated kinetic resolution of glycerol analogues: Efficient convergent route to both enantiomeric glycerol units. (8th June 2021)

• Record Type: Journal Article
• Authors: Aoyagi, Yutaka; Nomura, Shoko; Horiba, Karen; Shikano, Rina; Omura, Yumi; Omiya, Hiroko; Fukuzawa, Sanae; Yano, Reiko; Williams, Robert M.; Takeya, Koichi; Hitotsuyanagi, Yukio
• Is Part Of: Tetrahedron letters. Volume 73(2021)
• Publication Date: 2021-06-08
• Subjects: Kinetic resolution -- Lipase TL® -- Glycerol -- Efficient convergent route; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2021.153138
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Lipase TL®-mediated kinetic resolution of glycerols proceeded efficiently at −5 °C. High enantiomeric excess and quantitative yield. Efficient convergent route to both enantiomeric glycerol units. Abstract: In the presence of pyridine, at −5 °C, lipase TL®-mediated kinetic resolution of (±)-1-(( tert -butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-propan-2-ol was found to proceed efficiently to give the corresponding ( S )-alcohol and ( R )-acetate, each with high enantiomeric excess and in quantitative yield. The alcohol ( S )-1 and the acetate ( R )-2 -derived alcohol, ( R )-1, could be converted to the 1-protected glycerols with either of the stereochemistry by the choice of the deprotection of the protective groups.