Thermal and palladium-catalyzed [3 + 2] synthesis of cyclopentadienone acetals from cyclopropenone acetals and acetylenes

Hiroyuki Isobe; Sota Sato; Takatsugu Tanaka; Hidetoshi Tokuyama; Eiichi Nakamura

doi:10.1021/ol0483450

Thermal and palladium-catalyzed [3 + 2] synthesis of cyclopentadienone acetals from cyclopropenone acetals and acetylenes

Org Lett. 2004 Sep 30;6(20):3569-71. doi: 10.1021/ol0483450.

Authors

Hiroyuki Isobe¹, Sota Sato, Takatsugu Tanaka, Hidetoshi Tokuyama, Eiichi Nakamura

Affiliation

¹ Department of Chemistry, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

PMID: 15387550
DOI: 10.1021/ol0483450

Abstract

[reaction: see text] Substituted cyclopentadienone acetals (CPDAs) were synthesized by a thermal or palladium-catalyzed [3 + 2] cycloaddition reaction of a substituted cyclopropenone acetal to an electron-deficient acetylene. The synthesis afforded di-, tri-, and tetra-substituted CPDAs of considerable structural varieties that undergo Diels-Alder reaction to produce bicyclo[2.2.1]heptenes.