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Stereoselective synthesis towards unnatural proline-based amino acids

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Open access
Authors
Makhathini, S.
Das, S.
Singh, T.
Arvidsson, P.
Kruger, H.
Gunosewoyo, Hendra
Govender, T.
Naicker, T.
Date
2016
Type
Journal Article
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Abstract

A catalytic diastereoselective Mannich reaction promoted by chiral bifunctional urea-type organocatalysts has been developed. Treatment of N-Boc-3-ketoproline with N-Boc-aldimines under mild conditions afforded the corresponding unnatural proline based amino acid derivatives with excellent diastereoselectivities (up to 99:1) and enantioselectivities (up to 97% ee). The relative configuration of the chiral reaction products was deduced by the comparsion of the experimentally observed ECD spectra to that obtained theorectically.

Citation
Makhathini, S. and Das, S. and Singh, T. and Arvidsson, P. and Kruger, H. and Gunosewoyo, H. and Govender, T. et al. 2016. Stereoselective synthesis towards unnatural proline-based amino acids. Arkivoc. 2016 (3): pp. 134-144.
Source Title
Arkivoc
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DOI
Department
School of Pharmacy
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This open access article is distributed under the Creative Commons license http://creativecommons.org/licenses/by-nc/3.0/

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