Enantio- and diastereoselective tandem zn-promoted brook rearrangement/ene-allene carbocyclization reaction

Rozalia Unger; Fritz Weisser; Nicka Chinkov; Amnon Stanger; Theodore Cohen; Ilan Marek

doi:10.1021/ol9004036

Enantio- and diastereoselective tandem zn-promoted brook rearrangement/ene-allene carbocyclization reaction

Org Lett. 2009 Apr 16;11(8):1853-6. doi: 10.1021/ol9004036.

Authors

Rozalia Unger¹, Fritz Weisser, Nicka Chinkov, Amnon Stanger, Theodore Cohen, Ilan Marek

Affiliation

¹ Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry, and the Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, 32 000 Haifa, Israel.

PMID: 19290654
DOI: 10.1021/ol9004036

Abstract

The zinc-catalyzed addition of various alkynes to acylsilanes followed by a Zn-Brook rearrangement and either the Zn-ene-allene or Zn-yne-allene cyclization led to the enantio- and diastereoselective formation of carbocycles in a single-pot operation.