Michael addition of phthalimide and saccharin to enantiomerically pure diesters of BINOL and TADDOLs derivatives under microwave conditions

ANDREA COSTANTINO; SANDRA MANDOLESI; LILIANA KOLL

web - electronic conference

Conferencia; ECSOC-18 (18th International Electronic Conference on Synthetic Organic Chemistry); 2014

MDPI

One of the most important reactions in synthetic organic chemistry is the conjugate addition of nucleophilic species to the β-carbon of α,β-unsaturated systems. This process allows the construction of carbon backbones and very valuable from a synthetic point of view. Several attempts in the generation of β-amino derivatives have been reported and the aza-Michael addition reaction is widely recognized as one of the most important carbon-nitrogen bond?forming reaction in organic synthesis. Most of these products have special properties. Thus, this reaction provides a simple and appealing route toward the synthesis of N-alkyl derivatives of these compounds. In this work, we propose to study the aza-Michael reaction under microwave condition between saccharine and phtalimide with enantiomerically pure diesters of BINOL and TADDOLs derivatives. This methodology allowed us to obtain chiral di-addition products of great synthetic interest with good yields and relatively short reaction times.