A. Demir, Ozge Seşenoğlu, D. Ülkü
2004
Citations
0
Influential Citations
15
Citations
Journal
Helvetica Chimica Acta
Abstract
Starting from simple aromatic aldehydes and acetylfuran, (E)-1-(furan-2-yl)-3-arylprop-2-en-1-ones (2) were synthesized in high yields. Cyclopropanation of the CC bond with trimethylsulfoxonium iodide (Me3SO+I−) furnished (furan-2-yl)(2-arylcyclopropyl)methanones 3 in 90–97% yields. Selective conversion of cyclopropyl ketones to their (E)- and (Z)-oxime ethers 5 and oxazaborolidine-catalyzed stereoselective reduction of the CN bond followed by separation of the formed diastereoisomers, furnished (2-arylcyclopropyl)(furan-2-yl)methanamines 6 in optically pure form and high yield. Oxidation of the furan ring of (S,S,S)-, (S,R,R)-, (R,S,S)-, and (R,R,R)-6a afforded the four stereoisomers of α-(2-phenylcyclopropyl) glycine (1a).