Enantioselective synthesis of 2-(2-arylcyclopropyl)glycines: Conformationally restricted homophenylalanine analogs

Date

2004-01-01

Author

Demir, Ayhan Sıtkı
Sesenoglu, O
Ulku, D
Arici, C

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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 90-97% yields. Selective conversion of cyclopropyl ketones to their (E)- and (Z)-oxime ethers 5 and oxazaborolidine-catalyzed stercoselective 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 alpha-(2-phenylcyclopropyl) glycine (1a).

Subject Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis

URI

https://hdl.handle.net/11511/57503

Journal

HELVETICA CHIMICA ACTA

DOI

https://doi.org/10.1002/hlca.200490000

Collections

Department of Chemistry, Article

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Citation Formats

A. S. Demir, O. Sesenoglu, D. Ulku, and C. Arici, “Enantioselective synthesis of 2-(2-arylcyclopropyl)glycines: Conformationally restricted homophenylalanine analogs,” HELVETICA CHIMICA ACTA, pp. 106–119, 2004, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57503.