Stereocontrol in the synthesis of cyclic amino acids : a new ligand for directed hydrogenation through hydrogen bonding
A system for the directed hydrogenation of nitrogen heterocycles is described in which hydrogen is delivered cis to a hydroxymethyl group by a rhodium catalyst with a simple phosphine ligand. The chemistry is applied to the synthesis of the hygric acid moiety of lincomycin and the pipecolic acid moi...
Saved in:
| Main Authors: | , , , |
|---|---|
| Other Authors: | |
| Format: | Article |
| Language: | English |
| Published: |
2020
|
| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/141117 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Institution: | Nanyang Technological University |
| Language: | English |
| id |
sg-ntu-dr.10356-141117 |
|---|---|
| record_format |
dspace |
| spelling |
sg-ntu-dr.10356-1411172023-02-28T19:40:40Z Stereocontrol in the synthesis of cyclic amino acids : a new ligand for directed hydrogenation through hydrogen bonding Gandi, Vasudeva Rao Doan, Bao Nguyen Do Kasinathan, Sivarajan Bates, Roderick Wayland School of Physical and Mathematical Sciences Science::Chemistry Hydrogen Ligand A system for the directed hydrogenation of nitrogen heterocycles is described in which hydrogen is delivered cis to a hydroxymethyl group by a rhodium catalyst with a simple phosphine ligand. The chemistry is applied to the synthesis of the hygric acid moiety of lincomycin and the pipecolic acid moiety of Argatroban. A series of control experiments indicate that the stereoselectivity is a result of a combination of both coordination and hydrogen bonding. ASTAR (Agency for Sci., Tech. and Research, S’pore) Accepted version 2020-06-04T03:55:38Z 2020-06-04T03:55:38Z 2019 Journal Article Gandi, V. R., Doan, B. N. D., Kasinathan, S., & Bates, R. W. (2019). Stereocontrol in the synthesis of cyclic amino acids : a new ligand for directed hydrogenation through hydrogen bonding. Organic & Biomolecular Chemistry, 17(10), 2753-2758. doi:10.1039/C9OB00003H 1477-0520 https://hdl.handle.net/10356/141117 10.1039/C9OB00003H 17 2-s2.0-85062453859 10 17 2753 2758 en Organic & Biomolecular Chemistry © 2019 The Royal Society of Chemistry. All rights reserved. This paper was published in Organic & Biomolecular Chemistry and is made available with permission of The Royal Society of Chemistry. application/pdf |
| institution |
Nanyang Technological University |
| building |
NTU Library |
| continent |
Asia |
| country |
Singapore Singapore |
| content_provider |
NTU Library |
| collection |
DR-NTU |
| language |
English |
| topic |
Science::Chemistry Hydrogen Ligand |
| spellingShingle |
Science::Chemistry Hydrogen Ligand Gandi, Vasudeva Rao Doan, Bao Nguyen Do Kasinathan, Sivarajan Bates, Roderick Wayland Stereocontrol in the synthesis of cyclic amino acids : a new ligand for directed hydrogenation through hydrogen bonding |
| description |
A system for the directed hydrogenation of nitrogen heterocycles is described in which hydrogen is delivered cis to a hydroxymethyl group by a rhodium catalyst with a simple phosphine ligand. The chemistry is applied to the synthesis of the hygric acid moiety of lincomycin and the pipecolic acid moiety of Argatroban. A series of control experiments indicate that the stereoselectivity is a result of a combination of both coordination and hydrogen bonding. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Gandi, Vasudeva Rao Doan, Bao Nguyen Do Kasinathan, Sivarajan Bates, Roderick Wayland |
| format |
Article |
| author |
Gandi, Vasudeva Rao Doan, Bao Nguyen Do Kasinathan, Sivarajan Bates, Roderick Wayland |
| author_sort |
Gandi, Vasudeva Rao |
| title |
Stereocontrol in the synthesis of cyclic amino acids : a new ligand for directed hydrogenation through hydrogen bonding |
| title_short |
Stereocontrol in the synthesis of cyclic amino acids : a new ligand for directed hydrogenation through hydrogen bonding |
| title_full |
Stereocontrol in the synthesis of cyclic amino acids : a new ligand for directed hydrogenation through hydrogen bonding |
| title_fullStr |
Stereocontrol in the synthesis of cyclic amino acids : a new ligand for directed hydrogenation through hydrogen bonding |
| title_full_unstemmed |
Stereocontrol in the synthesis of cyclic amino acids : a new ligand for directed hydrogenation through hydrogen bonding |
| title_sort |
stereocontrol in the synthesis of cyclic amino acids : a new ligand for directed hydrogenation through hydrogen bonding |
| publishDate |
2020 |
| url |
https://hdl.handle.net/10356/141117 |
| _version_ |
1759853535882641408 |