This document presents information about Jacobson asymmetric epoxidation. It discusses the history, catalysts, mechanism, and applications of Jacobson asymmetric epoxidation. The catalyst uses a manganese (III) salen complex where tertiary butyl is the most effective substituent. There are three major pathways for the mechanism: concerted, free radical, and metallo oxetane. Jacobson asymmetric epoxidation is useful for synthesizing pharmaceutical drugs by forming chiral epoxides from cyclic and acyclic alkenes with 100% enantiopurity.

1. Presented By:
•Gandham Malasree
•Regd no: 620209502002
•Dept of Pharmaceutical Chemistry
AU COLLEGE OF PHARMACEUTICAL SCIENCES, VISAKHAPATNAM
Jacobson Asymmetric
Epoxidation

2. CONTENTS
Introduction
History
Catalysts
Synthesis of catalyst
Mechanism approach
Mechanism
Applications

3. INTRODUCTION
• It is also known as JACOBSON KATSUKI EPOXIDATION
What is epoxidation?

4. HISTORY

5. CATALYST
• Manganese (III) salen catalyst
R= alkyl, trialkyl etc.,
R= tertiary butyl is the most
effective

6. Active species in catalytic cycle: Oxo – managanese (V) salen

8. Synthesis of manganese salen complex

9. Jacobson and katsuki individually reported the catalysts
Katsuki catalyst

10. Mechanism approach

11. Mechanism
there are 3 major pathways
1. Concerted pathway
2. Free radical pathway
3. Metallo oxetane pathway

12. Mechanism

13. Applications 1

14. Application in process chemistry
2
Indene

15. • Forming a chiral epoxide is the key step for the synthesis of pharmaceutical
drugs.
• Cyclic and acyclic cis -1,2- disubstituted alkenes are epoxidized with 100%
enantiopurity.