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

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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

Citation Formats

A. S. Demir, C. Tanyeli, A. CAGİR, M. Nawaz Tahir, and D. Ulku, “Novel enantioselective synthesis of trans-α-(2-carboxycyclo-prop-1- yl)glycines: Conformationally constrained L-glutamate analogues,” Tetrahedron Asymmetry, vol. 9, no. 6, pp. 1035–1042, 1998, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/42597.