A Multimetallic Piano-Stool Ir-Sn-3 Catalyst for Nucleophilic Substitution Reaction of gamma-Hydroxy Lactams through N-Acyliminium Ions

作者：Maity Arnab Kumar; Roy Sujit^*

来源：Journal of Organic Chemistry, 2012, 77(6): 2935-2941.

DOI：10.1021/jo202359e

A multimetallic piano-stool complex [Cp*Ir-(SnCl3)(2){SnCl2(H2O)(2)}] (1) having Ir-Sn-3 motif has been synthesized from [Cp*IrCl2](2) and SnCl2. The multimetallic complex catalytically promotes the nucleophilic substitution reaction (here after alpha-amidoalkylation reaction) of gamma-hydroxylactams generated from phthalimidals to obtain decorated isoindolinones in excellent yields. Succinamidals, however, lead to the substituted pyrrolidinones (thermodynamic control product) via S(N)1-type path as well as eliminated pyrrolinones (kinetic control product) via an E1-type path, depending on the reaction parameters. A straightforward application of this methodology is to synthesize benzo-fused indolizidine alkaloid mimics.

• 出版日期2012-3-16