A solvent-free organocatalyzed intermolecular cyclization reaction starting from β-substituted γ-hydroxy-α,β-unsaturated esters and aryl isothiocyanates proceeds via an aza-Michael addition to provide previously unknown quaternary oxazolidine-2-thione β3 amino ester analogs. A panel of diversely-substituted esters was investigated, including β,γ-disubstituted examples which provided the target molecules with very high cis diastereoselectivity.
Solvent-Free Synthesis of Quaternary Oxazolidine-2-thione β3-Amino Ester Analogs
Soddu F.;Caboni P.;Secci F.;Frongia A.
Ultimo
2022-01-01
Abstract
A solvent-free organocatalyzed intermolecular cyclization reaction starting from β-substituted γ-hydroxy-α,β-unsaturated esters and aryl isothiocyanates proceeds via an aza-Michael addition to provide previously unknown quaternary oxazolidine-2-thione β3 amino ester analogs. A panel of diversely-substituted esters was investigated, including β,γ-disubstituted examples which provided the target molecules with very high cis diastereoselectivity.
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