Gold-catalyzed cascade cycloisomerization of 1,7-diyn-3,6-bis(propargyl carbonate)s: stereoselective synthesis of naphtho[b]cyclobutenes

Ming Chen; Jun Liu; Lu Wang; Xiaobo Zhou; Yuanhong Liu

doi:10.1039/c3cc44757j

Gold-catalyzed cascade cycloisomerization of 1,7-diyn-3,6-bis(propargyl carbonate)s: stereoselective synthesis of naphtho[b]cyclobutenes

Chem Commun (Camb). 2013 Oct 7;49(77):8650-2. doi: 10.1039/c3cc44757j.

Authors

Ming Chen¹, Jun Liu, Lu Wang, Xiaobo Zhou, Yuanhong Liu

Affiliation

¹ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling ling Lu, Shanghai 200032, P. R. China. [email protected].

PMID: 23949575
DOI: 10.1039/c3cc44757j

Abstract

Gold-catalyzed cycloisomerization of 1,7-diyn-3,6-bis(propargyl carbonate)s leads to a highly efficient and diastereoselective synthesis of functionalized naphtho[b]cyclobutenes. A cascade sequence involving gold-catalyzed double 3,3-rearrangement, 6π-electrocyclic reaction and a decarbonylative cyclization was proposed for this reaction.