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Enantioselective Synthesis of 2-(2-Arylcyclopropyl)glycines: Conformationally Restricted Homophenylalanine Analogs

✍ Scribed by Ayhan S. Demir; Özge Sesenoglu; Dincer Ülkü; Cengiz Arici

Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
199 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis

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 (Me~3~SO^+^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 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).

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