Stereoselective synthesis towards unnatural proline-based amino acids

Makhathini, S.; Das, S.; Singh, T.; Arvidsson, P.; Kruger, H.; Gunosewoyo, Hendra; Govender, T.; Naicker, T.

doi:10.3998/ark.5550190.p009.462

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Access Status

Open access

Authors

Makhathini, S.

Das, S.

Singh, T.

Arvidsson, P.

Kruger, H.

Gunosewoyo, Hendra

Govender, T.

Naicker, T.

Date

2016

Type

Journal Article

Metadata

Show full item record

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

DOI

10.3998/ark.5550190.p009.462

ISSN

1551-7004

School

School of Pharmacy

Remarks

This open access article is distributed under the Creative Commons license http://creativecommons.org/licenses/by-nc/3.0/

URI

http://hdl.handle.net/20.500.11937/21516

Collection

Curtin Research Publications

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.