jo0605039_si_001.pdf (464.14 kB)

New Approaches to Polysubstituted Pyrroles and γ-Lactams Based on Nucleophilic Addition of Ti(IV) Enolates Derived from α-Diazo-β-keto Carbonyl Compounds to N-Tosylimines

Download (464.14 kB)
journal contribution
posted on 21.07.2006, 00:00 by Changqing Dong, Guisheng Deng, Jianbo Wang
The Ti(IV) enolates derived from α-diazo-β-keto esters or ketones efficiently add to TiCl4-activated N-tosylimines to give δ-N-tosylamino substituted α-diazo-β-keto carbonyl compounds. The diazo decomposition of the addition products occurs under Rh2(OAc)4-catalyzed or photoinduced conditions to afford pyrrole or γ-lactam derivatives, both in high yields.