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Diastereoselective β-hydroxy vinylsulfone isomerizations.

G W O'Neil¹, T D Clark¹, A P Jones¹

¹Department of Chemistry, Western Washington University, Bellingham, WA 98225, USA. oneilg@wwu.edu.

Organic & Biomolecular Chemistry

|January 15, 2025

Summary

Vinylic phenylsulfones isomerize to allylic compounds using 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU). Reaction diastereoselectivity increases with steric bulk, favoring the erythro-isomer.

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Area of Science:

Organic Chemistry
Stereoselective Synthesis

Background:

Vinylic phenylsulfones are versatile synthetic intermediates.
Control of stereochemistry in isomerization reactions is crucial for complex molecule synthesis.

Purpose of the Study:

To investigate the diastereoselective isomerization of β-hydroxy vinylic phenylsulfones.
To explore the influence of substrate structure on reaction stereoselectivity and yield.

Main Methods:

Treatment of β-hydroxy vinylic phenylsulfones with 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU).
Analysis of diastereomeric ratios using Nuclear Magnetic Resonance (NMR) spectroscopy.
Isolation and yield determination of the allylic phenylsulfone products.

Main Results:

Diastereoselective isomerization to allylic phenylsulfones was achieved.
Stereoselectivity increased with the steric bulk of the substituent on the carbinol carbon, reaching >20:1 dr for tert-butyl.
Isolated yields ranged from 59-66%, with C-C bond cleavage as a competing pathway.

Conclusions:

DBU-mediated isomerization provides a stereoselective route to allylic 1,2-hydroxy phenylsulfones.
Steric effects play a significant role in controlling the diastereoselectivity of the isomerization.
The erythro-isomer is consistently favored, indicating a predictable stereochemical outcome.