一一一一

The palladium‐catalyzed cross‐dehydrogenative coupling followed by an intramolecular cyclization between arylquinazolinones and aldehydes is reported. This viable transformation provides a variety of novel substituted hydroxyisoindolo[1,2‐b]quinazolinone compounds in moderate to good yields.

The palladium‐catalyzed cross‐dehydrogenative coupling (CDC) followed by an intramolecular cyclization between arylquinazolinones and aldehydes has been described. This viable transformation provides a variety of novel substituted hydroxyisoindolo[1,2‐b]quinazolinone compounds in moderate to good yields. Additionally, the reaction is performed with toluene in place of benzaldehyde by using an excess amount of tert‐butyl hydroperoxide (TBHP) as the oxidant in good yield.

Abstract

The work reported within this paper describes an example of the application of bimetallic catalysts system in allylic substitution reactions. The development of new nucleophiles and the control of enantio‐ and diastereoselectivity are the main research topics in this area. An improvement in the reactivity and diastereoselectivity has been realized for the dual Ir/Cu catalyzed allylic alkylation of inactive prochiral nucleophiles, under mild reaction conditions. Furthermore, the choice of the metallacyclic iridium complex and chiral Cu‐Phox complex combination allows for access to all four stereoisomers from the same starting materials with excellent enantioselectivity and diastereoselectivity (up to >99% ee and >20:1 dr). Significantly, this method provides a stereodivergent access to 2‐amino‐3‐methylpent‐4‐acid ester, an important fragment for the synthesis of Halipeptin A.

Angewandte Chemie International Edition, EarlyView.

Advanced Synthesis &Catalysis, Volume 360, Issue 7, Page 1466-1472, April 3, 2018.