Diastereoselective 1,3-dipolar cycloaddition of pyrylium ylides with chiral enamides

Kirill Tchabanenko, Colleen Sloan, Yves-Mael Bunetel, Philip Mullen
2012 Organic and biomolecular chemistry  
Chiral enamides 5f-i were found to react with pyrylium ylides to give cycloadducts 6d-i in good yields with an excellent level of stereoselectivity. The chiral auxiliary was successfully removed on hydrogenolysis of compound 6f in continuous flow (H-Cube) resulting in the first asymmetric synthesis of complex amine 8.
doi:10.1039/c2ob07007c pmid:22517727 fatcat:wjlvfwo63jbdlckztzcci3ko7i