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- Title
Enantioselective Synthesis of 2-(2-Arylcyclopropyl)glycines: Conformationally Restricted Homophenylalanine Analogs.
- Authors
Ayhan S. Demir; Özge Sesenoglu; Dincer Ülkü; Cengiz Arici
- 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 C=C bond with trimethylsulfoxonium iodide (Me3SO+I-) furnished (furan-2-yl)(2-arylcyclopropyl)methanones 3 in 9097% yields. Selective conversion of cyclopropyl ketones to their (E)- and (Z)-oxime ethers 5 and oxazaborolidine-catalyzed stereoselective reduction of the C=N 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).
- Subjects
AROMATIC compounds; FURANS; ALDEHYDES; IODIDES
- Publication
Helvetica Chimica Acta, 2004, Vol 87, Issue 1, p106
- ISSN
0018-019X
- Publication type
Article