Projects per year
Abstract
The isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangement of N,N-diallyl allylic ammonium ylides is explored as a key part of a route to free functionalised α-amino esters and piperidines. The [2,3]-sigmatropic rearrangement proceeds with excellent diastereo- and enantiocontrol (>95:5 dr, up to 97% ee), with the resultant N,N-diallyl α-amino esters undergoing either mono- or bis-N-allyl deprotection. Bis-N-allyl deprotection leads to free α-amino esters, while the mono-deprotection strategy has been utilized in the synthesis of a target functionalised piperidine.
Original language | English |
---|---|
Pages (from-to) | 4138-4149 |
Number of pages | 12 |
Journal | Tetrahedron |
Volume | 73 |
Issue number | 29 |
Early online date | 30 Jan 2017 |
DOIs | |
Publication status | Published - 20 Jul 2017 |
Keywords
- [2,3]-rearrangement
- Isothiourea catalysis
- Allylic ammonium ylides
- Enantioselective catalysis
- α-amino esters
Fingerprint
Dive into the research topics of 'Isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangements of N,N-diallyl allylic ammonium ylides'. Together they form a unique fingerprint.Projects
- 3 Finished
-
RS Wolfson Merit Award: Developing Catalysis Research: New Reaction Discoveries and Practical Applications
Smith, A. D. (PI)
1/01/15 → 31/12/19
Project: Fellowship
-
-
ERC Starting Grant EnolCat: Emulating nature: Reaction diversity and understanding through asymmetric catalysis
Smith, A. D. (PI)
1/10/11 → 30/06/17
Project: Standard
Datasets
-
Data underpinning "Isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangements of N,N-diallyl allylic ammonium ylides"
Smith, A. D. (Creator) & West, T. H. (Contributor), University of St Andrews, 24 Aug 2016
DOI: 10.17630/f522b48d-ed02-42b3-a161-54687ea5af57
Dataset
File