Facial selectivity induced by N-aryl atropisomerism in benzonitrile oxide cycloadditions with 4-methylene-2-oxazolidinones

Harding, Sarah L.; Savage, G. Paul

doi:10.1039/c2ob25271f

Cited by 11 publications

(1 citation statement)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The synthetic applicability of these heterocycles has increased with the development of new methods for their construction . Functionalized 4‐methylene‐1,3‐oxazolidin‐2‐ones have also proven to be versatile synthons in the formation of diverse molecular systems …”

Section: Introductionmentioning

confidence: 99%

Enantiopure 4‐oxazolin‐2‐ones and 4‐methylene‐2‐oxazolidinones as chiral building blocks in a divergent asymmetric synthesis of heterocycles

et al. 2019

View full text Add to dashboard Cite

Enantiopure 3‐((R)‐ and 3‐((S)‐1‐phenylethyl)‐4‐oxazoline‐2‐ones were evaluated as chiral building blocks for the divergent construction of heterocycles with stereogenic quaternary centers. The N‐(R)‐ or N‐(S)‐1‐phenylethyl group of these compounds proved to be an efficient chiral auxiliary for the asymmetric induction of the 4‐ and 5‐positions of the 4‐oxazolin‐2‐one ring through thermal and MW‐promoted nucleophilic conjugated addition to Michael acceptors and alkyl halides. The resulting adducts were transformed via a cascade process into fused six‐membered carbo‐ and heterocycles. The structure of the reaction products depended on the electrophiles and reaction conditions used. Alternative isomeric 4‐methylene‐2‐oxazolidinones served as chiral precursors for a versatile and divergent approach to highly substituted cyclic carbamates. DFT quantum calculations showed that the formation of bicyclic pyranyl compounds was generated by a diastereoselective concerted hetero‐Diels‐Alder cycloaddition.

show abstract

Section: Introductionmentioning

confidence: 99%