Diastereofacial Selectivity in Intermolecular Nitrone Cycloadditions to Chiral Allyl Ethers. Application to Chiral Synthesis of Coniine

Article abstract of DOI:10.1016/0040-4039(92)80019-G

The intermolecular cycloadditions of a cyclic nitrone to chiral allyl ethers take place with erythro selectivity, where the degree of selectivity achieved is dependent upon the size of the alkyl substituent attached to the allylic chiral center, and these reactions are applied to the synthesis of optically active alkaloid coniine.