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| Author(s): |
Rafaela Costa Carmona
Total Authors: 1
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| Document type: | Master's Dissertation |
| Press: | São Paulo. |
| Institution: | Universidade de São Paulo (USP). Conjunto das Químicas (IQ e FCF) (CQ/DBDCQ) |
| Defense date: | 2013-02-22 |
| Examining board members: |
Alcindo Aparecido dos Santos;
Reinaldo Camino Bazito;
Kleber Thiago de Oliveira
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| Advisor: | Alcindo Aparecido dos Santos |
| Abstract | |
This masters thesis describes studies for the asymmetric version of A3 multicomponent reactions. Several methodologies were employed in order to obtain optically active propargylamines, which are versatile synthetic building blocks on the preparation of bioactive compounds. The work was divided into two parts. In the first part, we investigated the use of optically pure amines as starting materials for the A3-coupling reaction. In this case, we used the 2-methylpropan-2-sulfinamide as the main amine, however, the coupling product was not obtained, even under several reaction conditions. Other optically pure amines such as (S)-methylbenzylamine and amines derived from amino acids, were also tested. The yields and diastereomeric excess were satisfactory when amines derived from amino acids were employed, especially when the methyl ester of L-poline was used as amine source, which led to the formation of the product in good yield and diastereoisomeric ratio. In the second part we studied the use of chiral auxiliaries in the A3-coupling reaction to induce the asymmetry. Therefore, several compounds were tested as optically pure oxazolines and L-proline derivatives. (AU) | |
| FAPESP's process: | 11/03244-2 - Asymmetric strategies in A-3 coupling eactions |
| Grantee: | Rafaela Costa Carmona |
| Support Opportunities: | Scholarships in Brazil - Master |