Mislow–Evans rearrangement
The Mislow–Evans rearrangement is a
General reaction scheme
The reaction is a powerful way to create particular
diastereoselective and the chirality
at the sulphur atom can be transmitted to the carbon next to the oxygen in the product.
The sulfoxide 1 reagent can be generated easily and
benzyl
Mechanism
A proposed mechanism is shown below:[4]
The mechanism starts with an allylic sulfoxide 1 which undergoes a thermal
sulfenate ester 2. This can be cleaved using a thiophile, such as phosphite ester, which leaves the allylic alcohol 3 as the product.[5]
Scope
The reaction has general application in the preparation of trans-allylic alcohols.[6] Douglass Taber used the Mislow–Evans rearrangement in the synthesis of the hormone prostaglandin E2.[4]
References
- .
- .
- ISBN 978-3-540-30030-4.
- ^ ISBN 9780124297852.
- .
- ISBN 978-0-471-70450-8