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Asymmetric Baylis Hillman reaction

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).