PtCl₄‐Catalyzed Domino Synthesis of Fused Bicyclic Acetals

Abstract

At sixes and sevens: The synthesis of [4.2.1]- and [3.2.1]-fused bicyclic acetals by an intramolecular double alkoxylation of alkyne diols is reported. The course of the reaction depends on the substitution of the triple bond. Terminal alkynes give the [3.2.1]bicyclic product by a 6-exo pathway, whereas aryl alkynes undergo almost exclusively a 7-endo cyclization to give the [4.2.1]bicycles (see scheme, Ts=toluene-4-sulfonyl). Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2008/z704595_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.