Year: 2014
Type: dissertation
Abstract: The use of chemoenzymatic resolutions for the separation of racemic mixtures is a common route that affords enantiomerically pure compounds. Finding novel and selective protecting group strategies to facilitate the resolution of 1,2-diol systems remains challenging. The use of tin(II) halide-catalyzed reactions with diazo[bis(4-methylphenyl)]methane with racemic vicinal 1,2-diols gives a mixture of the corresponding 1- and 2-benzhydryl ethers with a regiopreference for the primary hydroxyl group in good overall yield. Tin(II) chloride and Tin(II) bromide were evaluated as catalyst for the regioselective introduction of bis(4-methylphenyl)methane ethers from the corresponding diazocompound. Following partial protection, five commercially available lipases were evaluated for their ability to resolve 1-benzhydryl ethers of 1,2-diol systems. Subsequent kinetic resolution with immobilized lipase from Pseudomonas cepacia afforded the corresponding (2R) acetate and (2S) alcohol. De-acylation of the 2R diol affords the corresponding free alcohol.
Source: Skemman
Author: Sean Michael Scully
Language: English
Subfield: Molecular Biology
Domain: Life Sciences
Open Access status: green
Funder: Háskólinn á Akureyri
OpenAlex ID: W1575503658