Condition‐Directable Reaction: Regio‐ and Stereoselective Elimination of 2,3‐Dibromo‐2‐methylpropyl Phenyl Sulfone via Base‐solvent Selection

Abstract

Diversity‐oriented organic synthesis is an important approach for combinatorial chemistry and drug discovery. An example of this approach is selective elimination of 2,3‐dibromo‐2‐methylpropyl phenyl sulfone 5 to potentially useful vinyl sulfones 6 E/Z and vinyl bromides 7 E/Z , which is achieved by choosing reaction conditions.

This work was done during my graduate research under the guidance of Philip L. Fuchs in the Department of Chemistry at Purdue University, West Lafayette, Indiana, USA.

Keywords:

• Diversity-oriented
• reaction condition-directable
• regio- and stereoselective
• elimination
• vinyl sulfones
• vinyl bromides
• dibromo
• phenyl sulfone

Acknowledgment

I am grateful to Philip L. Fuchs for his guidance during this research and encouraging me to write this manuscript, John F. Hansen for his valuable suggestions for the preparation of this manuscript, and Douglas Lantrip for his support, especially his analytical support.

Notes

This work was done during my graduate research under the guidance of Philip L. Fuchs in the Department of Chemistry at Purdue University, West Lafayette, Indiana, USA.