Sugar-based Catalyst for the Highly Diastereoselective Desymmetrization of dbas

Sugar-based Catalyst for the Highly Diastereoselective Desymmetrization of dbas

Gonçalves, Jaqueline R.; Duarte, Talita N.; Pinheiro, Danielle L. J.; Amarante, Giovanni W.

Abstract:

Carbohydrates as catalysts have been explored by several research groups due to structural diversity and their chirality. Particularly in the field of organocatalysis they appear as alternative in the synthesis of different catalysts with different backbones. Recently, we described a diastereoselective Michael addition between enones and azlactones by using (+/-)-CSA as a catalyst. In this diastereoselective version only unfunctionalized dibenziledeno acetone (dba) was described. Thus, in this communication we show our results on a Bronsted acid catalyzed stereoselective desymmetrization of dbas.

Carbohydrates as catalysts have been explored by several research groups due to structural diversity and their chirality. Particularly in the field of organocatalysis they appear as alternative in the synthesis of different catalysts with different backbones. Recently, we described a diastereoselective Michael addition between enones and azlactones by using (+/-)-CSA as a catalyst. In this diastereoselective version only unfunctionalized dibenziledeno acetone (dba) was described. Thus, in this communication we show our results on a Bronsted acid catalyzed stereoselective desymmetrization of dbas.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_201392145231

Referências bibliográficas

• [1] 1 Ávila, E. P.; Amarante, G. W. ChemCatChem 2012, 4, 1713.
• [2] 2 Ávila, E. P.; De Mello, A. C.; Diniz, R.; Amarante, G. W. Eur. J. Org. Chem. 2013, 10, 1881.

Como citar:

Gonçalves, Jaqueline R.; Duarte, Talita N.; Pinheiro, Danielle L. J.; Amarante, Giovanni W.; "Sugar-based Catalyst for the Highly Diastereoselective Desymmetrization of dbas", p-109-109. 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_201392145231