Stereoselective synthesis towards unnatural proline-based amino acids
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 diastereo...
| Main Authors: | , , , , , , , |
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| Format: | Journal Article |
| Published: |
2016
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| Online Access: | http://hdl.handle.net/20.500.11937/21516 |
| _version_ | 1848750611742326784 |
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| author | Makhathini, S. Das, S. Singh, T. Arvidsson, P. Kruger, H. Gunosewoyo, Hendra Govender, T. Naicker, T. |
| author_facet | Makhathini, S. Das, S. Singh, T. Arvidsson, P. Kruger, H. Gunosewoyo, Hendra Govender, T. Naicker, T. |
| author_sort | Makhathini, S. |
| building | Curtin Institutional Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T07:39:35Z |
| format | Journal Article |
| id | curtin-20.500.11937-21516 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T07:39:35Z |
| publishDate | 2016 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-215162017-09-13T13:52:23Z Stereoselective synthesis towards unnatural proline-based amino acids Makhathini, S. Das, S. Singh, T. Arvidsson, P. Kruger, H. Gunosewoyo, Hendra Govender, T. Naicker, T. 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. 2016 Journal Article http://hdl.handle.net/20.500.11937/21516 10.3998/ark.5550190.p009.462 fulltext |
| spellingShingle | Makhathini, S. Das, S. Singh, T. Arvidsson, P. Kruger, H. Gunosewoyo, Hendra Govender, T. Naicker, T. Stereoselective synthesis towards unnatural proline-based amino acids |
| title | Stereoselective synthesis towards unnatural proline-based amino acids |
| title_full | Stereoselective synthesis towards unnatural proline-based amino acids |
| title_fullStr | Stereoselective synthesis towards unnatural proline-based amino acids |
| title_full_unstemmed | Stereoselective synthesis towards unnatural proline-based amino acids |
| title_short | Stereoselective synthesis towards unnatural proline-based amino acids |
| title_sort | stereoselective synthesis towards unnatural proline-based amino acids |
| url | http://hdl.handle.net/20.500.11937/21516 |