1089672-01-4Relevant academic research and scientific papers
Asymmetric Annulation of Donor-Acceptor Cyclopropanes with Dienes
Xu, Hao,Hu, Jiang-Lin,Wang, Lijia,Liao, Saihu,Tang, Yong
, p. 8006 - 8009 (2015)
An efficient [4 + 3] cycloaddition reaction of D-A cyclopropanes with dienes has been successfully developed. The reaction proceeds well with various dienolsilyl ethers in the presence of Lewis acid, delivering a variety of cycloheptenes and [n,5,0]carbobicycles with excellent stereoselectivity. The asymmetric version of this reaction is also realized using a newly designed chiral Cy-TOX ligand, providing a new approach to access optically active cycloheptenes and [n,5,0]carbobicycles. Mechanisic study reveals that the reaction involves a stepwise pathway, which undergoes an unusual ring opening of five-membered [3 + 2] intermediate and sequential intramolecular cyclization to afford the thermodynamically stable [4 + 3] annulation product.
