Stereoselective cyclopropanations of amino-acid derived enones
2020
Anwar, Avraz | Kerns, Holli | Orr, Taylor | Byrd, Jonathan | Fitzsimonds, Zackary | Dunlap, Norma
Stereoselective cyclopropanation of a series of amino acid-derived enones to afford cyclopropyl keto-esters is reported, using a Michael-induced ring closure. The use of quinine and quinidine ether catalysts in the cyclopropanation step afforded the cyclopropyl keto-esters with high stereoselectivity. Results follow a consistent pattern, with the pseudoenantiomeric catalysts leading to opposite stereoselectivity, allowing for synthesis of either the syn or anti diastereomers.
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