Synlett 2016; 27(19): 2716-2720
DOI: 10.1055/s-0036-1588306
letter
© Georg Thieme Verlag Stuttgart · New York

2-Carboxythioester-1,3-dithiane: A Functionalized Masked Carbonyl Nucleophile for the Organocatalytic Enantioselective Michael Addition to Enones

Elisabetta Massolo
a   Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy   eMail: maurizio.benaglia@unimi.it
,
Davide Brenna
a   Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy   eMail: maurizio.benaglia@unimi.it
,
Franco Cozzi
a   Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy   eMail: maurizio.benaglia@unimi.it
,
Laura Raimondi
a   Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy   eMail: maurizio.benaglia@unimi.it
,
Nicoletta Gaggero
b   Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, Via Mangiagalli 25, 20133 Milano, Italy
,
Maurizio Benaglia*
a   Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy   eMail: maurizio.benaglia@unimi.it
› Institutsangaben
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Publikationsverlauf

Received: 02. Mai 2016

Accepted after revision: 08. August 2016

Publikationsdatum:
31. August 2016 (online)


Dedicated to Professor Achille Umani Ronchi for his 80th birthday

Abstract

An S-(2,2,2-trifluoroethyl) 1,3-dithiane-2-carbothioate has been successfully employed as acyl anion synthon in the organocatalytic enantioselective addition to enones promoted by quinine- and quinidine-derived tertiary/primary diamines. By proper selection of a co-catalyst and by optimization of the reaction parameters, convenient experimental conditions were found that allowed to obtain the highly functionalized products in up to 90% yield and 98% ee in short reaction times. These compounds, featuring selectively removable functionalities, proved to be versatile synthetic intermediates, which could be transformed into different derivatives without any erosion of the stereochemical integrity of the molecules.

Supporting Information

 
  • References and Notes

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