Brønsted Acid Catalyzed Azlactone Ring Opening With a Wide Range Substratre Scope

Brønsted Acid Catalyzed Azlactone Ring Opening With a Wide Range Substratre Scope

Pereira, Adriane A.; Castro, Pedro P. de; Mello, Amanda C. de; Amarante, Giovanni W.

Abstract:

Azlactones are basically protected amino acids which can be used in the synthesis of natural products. Our research group has been explored the potential of these heterocycles as nucleophiles in the presence of Michael acceptors. In the other hand, it is obvious the presence of two electrophile sites which can react in the presence of different nucleophiles. This strategy is very important since it could be applied in peptide synthesis. Recently, Wang and co-workers described a Brønsted acid as a catalyst for the kinect dynamic resolution following by ring opening of azlactones in the presence of a nucleophile. However, a few azlactone rings and only a special alcohol were well tolerated in the optimized reaction condition. Thus, in this communication it is showed the (+/-)- camphorsulfonic acid (CSA) as effective Brønsted acid catalyst for the azlactone ring opening in the presence of different nucleophiles.

Azlactones are basically protected amino acids which can be used in the synthesis of natural products. Our research group has been explored the potential of these heterocycles as nucleophiles in the presence of Michael acceptors. In the other hand, it is obvious the presence of two electrophile sites which can react in the presence of different nucleophiles. This strategy is very important since it could be applied in peptide synthesis. Recently, Wang and co-workers described a Brønsted acid as a catalyst for the kinect dynamic resolution following by ring opening of azlactones in the presence of a nucleophile. However, a few azlactone rings and only a special alcohol were well tolerated in the optimized reaction condition. Thus, in this communication it is showed the (+/-)- camphorsulfonic acid (CSA) as effective Brønsted acid catalyst for the azlactone ring opening in the presence of different nucleophiles.

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DOI: 10.5151/chempro-15bmos-BMOS2013_201392142048

Referências bibliográficas

• [1] 1 Ávila, E. P.; de Mello, A. C.; Diniz, R.; Amarante, G. W. Eur. J. Org. Chem. 2013, 1881.
• [2] 2 Wang, C.; Luo, H. W.; Gong, L. Z. Synlett, 2011, 992.

Como citar:

Pereira, Adriane A.; Castro, Pedro P. de; Mello, Amanda C. de; Amarante, Giovanni W.; "Brønsted Acid Catalyzed Azlactone Ring Opening With a Wide Range Substratre Scope", p-107-107. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_201392142048