Singlet oxygen: From discovery to natural and biologically active product synthesis November, 8-15-22-28 th 2005 By Isabelle Bonnaventure Literature Meeting.

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Presentation transcript:

Singlet oxygen: From discovery to natural and biologically active product synthesis November, th 2005 By Isabelle Bonnaventure Literature Meeting

Presentation Outlook

Discovery of 1 O 2 and use as a reagent

Properties of 1 O 2

Generation of 1 O 2

Reaction Overview

Ene reaction: Introduction

Ene reaction: Mechanism

Ene reaction: “cis effect”

Ene reaction: “cis effect” in styrene derivatives

Ene reaction: large group non-bonded effect

Ene reaction: bulky subtituents

Ene reaction: gem dimethyl/diethyl trisubstituted olefins

Ene reaction: hydroxyl group directing effect

Ene reaction: EWG at vinylic and allylic position

Ene reaction: cyclic molecules

Ene reaction: diastereoselectivity?

Comparison with other  -oxidation methods

[4+2] cycloaddition

[2+2] cycloaddition

[4+2], [2+2] cycloaddition or ene reaction ?

Ene reaction: application

[4+2] cycloaddition: application

[2+2] cycloaddition: application

Conclusion

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