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Novel enantioselective synthesis of trans-α-(2-carboxycyclo-prop-1- yl)glycines: Conformationally constrained L-glutamate analogues
Date
1998-03-27
Author
Demir, Ayhan Sıtkı
Tanyeli, Cihangir
CAGİR, Ali
Nawaz Tahir, M.
Ulku, Dincer
Metadata
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This work is licensed under a
Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License
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D- and L-alpha-(2-carboxycycloprop-1-yl)glycines were synthesized from trans-1,3-di(2-furyl)propenane. Conversion of the double bond to a cyclopropane is followed by-the formation of an oxime ether. Enantioselective reduction of the oxime ether, separation of diastereomers and oxidation of the furane rings gave enantiomerically pure D- and L-CCG I and CCG II. The structure of oxime 7b was determined by X-ray crystal structure analysis. The key step is the oxazaborolidine catalyzed enantioselective conversion of oxime ethers to amines. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
Subject Keywords
Chirally modified borohydrides
,
Amino-acid receptors
,
Rat spinal-cord
,
Reduction
,
Ketones
,
Borane
,
Cis-alpha-(carboxycyclopropyl)glycines
,
Targets
,
Potentiation
,
Alcohols
URI
https://hdl.handle.net/11511/42597
Journal
Tetrahedron Asymmetry
DOI
https://doi.org/10.1016/s0957-4166(98)00061-5
Collections
Department of Chemistry, Article