| dc.contributor |
Massachusetts Institute of Technology. Department of Chemistry |
|
| dc.contributor |
Zhu, Shaolin |
|
| dc.contributor |
Niljianskul, Nootaree |
|
| dc.contributor |
Buchwald, Stephen Leffler |
|
| dc.creator |
Zhu, Shaolin |
|
| dc.creator |
Niljianskul, Nootaree |
|
| dc.creator |
Buchwald, Stephen Leffler |
|
| dc.date |
2017-07-06T14:54:04Z |
|
| dc.date |
2017-07-06T14:54:04Z |
|
| dc.date |
2016-02 |
|
| dc.date |
2015-08 |
|
| dc.date.accessioned |
2023-03-01T18:09:28Z |
|
| dc.date.available |
2023-03-01T18:09:28Z |
|
| dc.identifier |
1755-4330 |
|
| dc.identifier |
1755-4349 |
|
| dc.identifier |
http://hdl.handle.net/1721.1/110483 |
|
| dc.identifier |
Zhu, Shaolin, Nootaree Niljianskul, and Stephen L. Buchwald. “A Direct Approach to Amines with Remote Stereocentres by Enantioselective CuH-Catalysed Reductive Relay Hydroamination.” Nature Chemistry (2016): n. pag. |
|
| dc.identifier |
https://orcid.org/0000-0003-3875-4775 |
|
| dc.identifier.uri |
http://localhost:8080/xmlui/handle/CUHPOERS/278966 |
|
| dc.description |
Amines with remote stereocentres (stereocentres that are three or more bonds away from the C–N bond) are important structural elements in many pharmaceutical agents and natural products. However, previously reported methods to prepare these compounds in an enantioselective manner are indirect and require multistep synthesis. Here, we report a copper-hydride-catalysed, enantioselective synthesis of γ- or δ-chiral amines from readily available allylic alcohols, esters and ethers using a reductive relay hydroamination strategy (a net reductive process in which an amino group is installed at a site remote from the original carbon–carbon double bond). The protocol was suitable for substrates containing a wide range of functional groups and provided remote chiral amine products with high levels of regio- and enantioselectivity. Sequential amination of substrates containing several carbon–carbon double bonds could be achieved, demonstrating the high chemoselectivity of this process. |
|
| dc.description |
National Institutes of Health (U.S.) (Award GM58160) |
|
| dc.format |
application/pdf |
|
| dc.language |
en_US |
|
| dc.publisher |
Nature Publishing Group |
|
| dc.relation |
http://dx.doi.org/10.1038/nchem.2418 |
|
| dc.relation |
Nature Chemistry |
|
| dc.rights |
Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. |
|
| dc.source |
PMC |
|
| dc.title |
A direct approach to amines with remote stereocentres by enantioselective CuH-catalysed reductive relay hydroamination |
|
| dc.type |
Article |
|
| dc.type |
http://purl.org/eprint/type/JournalArticle |
|