Journal
CHIRALITY
Volume 31, Issue 9, Pages 719-749Publisher
WILEY
DOI: 10.1002/chir.23109
Keywords
(R)- and (S)-1-phenylethylamine; 4-methylene-2-oxazolidinones; 4-oxazolin-2-ones; hetero-Diels-Alder reaction; microwave irradiation
Funding
- National Laboratory of the Universidad de Guanajuato [260373]
- SIP-IPN [20181307, 20171928, 20160567, 20195287, 20181332, 20170902, 20160791, 20195228, 20180198]
- CONACYT [282033, A1-S-17131, 178319, 83446]
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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.
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