Stereoselective intramolecular nicholas reaction using epoxides as nucleophiles.

Autor: Crisóstomo FR; Instituto Universitario de Bio-Orgánica 'Antonio González', Universidad de La Laguna,C/Astrofísico Francisco Sánchez, 2, 38206 La Laguna, Tenerife, Spain., Martín T, Martín VS
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2004 Feb 19; Vol. 6 (4), pp. 565-8.
DOI: 10.1021/ol0363570
Abstrakt: [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.
Databáze: MEDLINE