Stereoselective intramolecular nicholas reaction using epoxides as nucleophiles

Org Lett. 2004 Feb 19;6(4):565-8. doi: 10.1021/ol0363570.

Abstract

[reaction: see text] The intramolecular nucleophilic attack of the epoxides on the exo-Co(2)(CO)(6)-propargylic cations provided cyclic ethers in good yields. The use of substrates with stereochemically defined oxiranes provided polysubstituted tetrahydropyrans and oxepanes with a high degree of stereocontrol. The cyclization is sensitive to the nature of the protecting group used at the primary alcohol, the use of tert-butyl carbonates being highly effective in terms of regioselectivity and yields.