Camphor Derivatives in Asymmetric Cycloadditions and Rearrangements

Abstract

Camphor-derived α,β-unsaturated oxazolines and oxazoline N-oxides are, respectively, useful dienophiles and dipolarophiles in [2+4] and [2+3] diastereoselective cycloadditions. The scope and limitations of these two reactions as well as their synthetic applications in the synthesis of various natural products are discussed. The Account also covers σ-[2,3] rearrangement of oxazoline N-oxide, which gives a new insight into the mechanism of this type of reaction. Finally, recent developments in Diels-Alder organocatalyzed cycloaddition with camphor-derived sulfonylhydrazines are also discussed.