Catalyst-Controlled [3 + 2] and [4 + 2] Annulations of Oximes with Propargyl Alcohols: Divergent Access to Indenamines and Isoquinolines

• DOI: 10.1021/acs.orglett.7b03546
• Publication Date: 2017-12-14T17:47:17Z
• Authors: Wanchun Gong; Zhi Zhou; Jingjing Shi; Bo Wu; Biyun Huang; Wei Yi
• Keywords: Propargyl

Rhodium(III)- and iridium(III)-catalyzed C-H activation of oximes coupling with propargyl alcohols is discussed. Depending on the catalyst, reaction pathway switched between [3 + 2] [4 annulations, thus giving divergent access to indenamines isoquinolines in a one-pot atom-economical manner. The hydroxyl group tertiary alcohol substrate was found be crucial controlling chemoselectivity. Five-membered rhodacycle iridacycle intermediates have also been identified for mechanism hypotheses.