Synthesis of trisubstituted alkenes via olefin cross-metathesis.

New aspects of the Ireland and related Claisen rearrangements

This article surveys variants of the Claisen rearrangement that are of general use in stereoselective organic synthesis. Recent results concerning the influence of steric and electronic parameters on transition state geometries are highlighted. The impact of the Claisen methodology in modern synthetic strategy and its application for the preparation of highly functionalized derivatives is exemplified.

7.2 – Claisen Rearrangements

Total Synthesis of Ambruticin

Total synthesis of (+)-ambruticin S

The Stereoselective Ciaisen rearrangement of a series of tertiary allylic sulphone esters is reported.

The stereocontrolled Claisen rearrangement of tertiary allylic sulphone esters: stereoselective formation of trisubstituted double bonds

In the Claisen rearrangement of a series of diastereoisomeric tertiary allylic alcohols the stereoselectivity is found to be dependent upon the chiral centre adjacent to the allylic alcohol.

Ian H. Wallace

Papers

The stereocontrolled Claisen rearrangement of tertiary allylic sulphone esters: stereoselective formation of trisubstituted double bonds

Stereochemical control in the Claisen rearrangement: influence of an adjacent chiral centre

The Stereocontrolled Claisen Rearrangement of Tertiary Allylic Sulfone Esters: Stereoselective Formation of Trisubstituted Double Bonds.

Stereochemical Control in the Claisen Rearrangement: Influence of an Adjacent Chiral Centre.