ABHR · Asymmetric Baylis Hillman reaction
FP6 — Marie Curie Actions (Human Resources and Mobility)
- Duration
- 2006-01-15 → 2007-09-14
- EU contribution
- €228,760
- Participants
- 1
- Scheme
- EIF
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Results in brief
Final Activity Report Summary - ABHR (Asymmetric Baylis Hillman reaction)
The aim of this project is the development of an efficient and enantioselective Baylis-Hillman reaction. With this objective in mind we tried to achieve it through three different strategies: 1) Using L-Proline as catalyst and acetic acid as co-catalyst (chiral proton transfer), tetrahydrothiophene as nucleophile and DMSO as solvent we have been able to obtain Baylis Hillman adducts but only with low enantioselectivity (er 66 : 34). 2) Asymmetric Baylis Hillman type reaction using the Aggarwal sulfide from the corresponding enones and acetals under Lewis acid conditions, we obtained the Baylis Hillman adducts with low nantioselectivity (er 45 : 55). 3) The Baylis Hillman type reaction of N,O-aminals with acrylates. Using the Evans auxiliary, we have been able to couple unsaturated oxazolidinones with N,O-aminals with good levels of selectivity (er 100 : 0).
Data: CORDIS, © European Union
Project objective
In this project, we report a novel approaches to the asymmetric Baylis-Hillman (BH) reactions. The study (scope and limitations) of this new variant of the B-H reaction, leads the way to the development of a useful and broadly applicable methodology in the future. In this way, we propose a new strategy for the design of chiral catalysts derived from Proline, with the aim to develop a catalytic asymmetric version of the Baylis-Hillman reaction.
Original text from CORDIS.
Participants
- UNIVERSITY OF BRISTOL · BRISTOL, CLIFTONCoordinatorUnited Kingdom
Links
Data: CORDIS, © European Union