Base‐Dependent Stereodivergent Intramolecular Aza‐Michael Reaction: Asymmetric Synthesis of 1, 3‐Disubstituted Isoindolines. Issue 35 (12th July 2013)

• Record Type: Journal Article
• Authors: Fustero, Santos; Herrera, Lidia; Lázaro, Ruben; Rodríguez, Elsa; Maestro, Miguel A.; Mateu, Natalia; Barrio, Pablo
• Is Part Of: Chemistry. Volume 19:Issue 35(2013)
• Page Start: 11776
• Page End: 11785
• Publication Date: 2013-07-12
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201301591
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The nucleophilic addition (A_N) / intramolecular aza‐Michael reaction (IMAMR) process on Ellman's <italic>tert</italic>‐butylsulfinyl imines, bearing a Michael acceptor in the <italic>ortho</italic> position, is studied. This reaction affords 1, 3‐disubstituted isoindolines with a wide range of substituents in good yields and diastereoselectivities. Interestingly, careful choice of the base for the aza‐Michael step allows either the <italic>cis</italic> or the <italic>trans</italic> diastereoisomers to be exclusively obtained. This stereodivergent cyclization has enabled the synthesis of <italic>C</italic>₂‐symmetric bisacetate‐substituted isoindolines. In addition, bisacetate isoindolines bearing two well‐differentiated ester moieties are also noteworthy because they may allow for the orthogonal synthesis of β, β′‐dipeptides using a single nitrogen atom as a linchpin.</p> </abstract>