6533b82efe1ef96bd12929fe
RESEARCH PRODUCT
Base-Dependent Stereodivergent Intramolecular Aza-Michael Reaction: Asymmetric Synthesis of 1,3-Disubstituted Isoindolines
Ruben LazaroMiguel A. MaestroNatalia MateuSantos FusteroPablo BarrioElsa RodríguezLidia Herrerasubject
chemistry.chemical_classificationheterocyclesOrtho positioncyclizationNucleophilic additionBase (chemistry)Stereochemistryasymmetric synthesisOrganic ChemistryEnantioselective synthesisDiastereomerGeneral ChemistryCatalysischiral auxiliarieschemistryNitrogen atomIntramolecular forceMichael reactionaza-Michael additiondescription
The nucleophilic addition (A(N)) / intramolecular aza-Michael reaction (IMAMR) process on Ellman's tert-butylsulfinyl imines, bearing a Michael acceptor in the ortho 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 cis or the trans diastereoisomers to be exclusively obtained. This stereodivergent cyclization has enabled the synthesis of C2-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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2013-01-01 | Chemistry - A European Journal |