Year: 2025
Type: article
Abstract: Vinylic phenylsulfones containing a β-hydroxyl stereocenter undergo a diastereoselective isomerization to the corresponding allylic isomer upon treatment with 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU). Diastereoselectivity of this reaction increases with increasing size of the group attached to the carbinol carbon (up to >20:1 d.r. with a tert-butyl). Isolated yields of the isomerized allylic 1,2-hydroxy phenylsulfone products were comparable among the different vinylsulfones tested (59-66%). The major competing pathway was a C-C bond cleavage process, proposed to occur after the initial isomerization event. The sense of diastereoselection was consistent among all substrates investigated, in favor of the erythro-isomer based on NMR analysis.
Source: Organic & Biomolecular Chemistry
DOI: 10.1039/d4ob01781a
Authors: G. W. O'Neil, T. D. Clark, A. P. Jones, C. Wallace, D. M. Carnahan, H. Crockett
Institution: Western Washington University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W4406270424