Dezembro 2013 vol. 1 num. 2 - Brazilian Meeting on Organic Synthesis 2013

Abstract - Open Access.

Idioma principal

The Baylis-Hillman reaction: Our vision and experience

Basavaiah, D. ;

Abstract:

To meet the demands of emerging trends, the present day organic chemistry emphasizes the need for discovering new reactions or strategies for construction of carbon-carbon bonds mainly involving the concepts of atom–economy, organo-catalysis, and easy generation of useful molecules containing proximal functional groups for assembling the required carbon frameworks. The Baylis-Hillman (also known as the Morita-Baylis-Hillman) reaction is one such organocatalytic atom-economy reaction developed in recent years, for the construction of carbon-carbon bonds leading to the production of diverse classes of molecules having several functional groups in close proximity. It is a three component atom–economy carbon-carbon bond forming reaction between the α-position of activated alkenes and electrophiles under the influence of a catalyst (most commonly an organic catalyst). These multi-functional molecules, which are usually known as Baylis-Hillman (BH) adducts, showed enormous utility in many directions of synthetic and mechanistic chemistry, clearly demonstrating the power of proximity of the functional groups in molecules. We have been systematically working on various aspects of this reaction for the last 29 years with the main objective of understanding and developing the Baylis-Hillman reaction as a useful and powerful tool in synthetic chemistry. We have in fact, contributed significantly to its growth with respect to all the three essential components. We have also demonstrated very high applicability and potential of the Baylis-Hillman adducts in a number of organic transformations leading to the synthesis of different carbocyclic and heterocyclic compounds, including bioactive molecules. This talk will present our vision, objectives, and endeavors towards the development of this reaction as a source of opportunities, challenges and creativity in synthetic chemistry keeping its applications as the primary goal.

Abstract:

Download (PDF)

Palavras-chave: Baylis-Hillman reaction, Organocatalysis, Atom economy,

Palavras-chave:

DOI: 10.5151/chempro-15bmos-13-BASAVAIAH_ABSTRACT_DB-15th_BMOS

Referências bibliográficas
  • [1] 1Basavaiah, D.; Sahu, B. C. Chimia 2013, 67, 8.
  • [2] 2Wei, Y.; Shi, M. Chem. Rev. 2013, 113, 6659.
  • [3] 3 Liu, T-Y.; Xie, M.; Chen, Y-C. Chem. Soc. Rev. 2012, 41, 4101.
  • [4] 4Basavaiah, D.; Veeraraghavaiah, G. Chem. Soc. Rev. 2012, 41, 68.
  • [5] 5Basavaiah, D.; Reddy, B. S.; Badsara, S.S. Chem. Rev. 2010, 110, 5447.
  • [6] 6Singh, V.; Batra, S. Tetrahedron 2008, 64, 4511.
  • [7] 7Basavaiah, D.; Rao, K. V.; Reddy, R. J. Chem. Soc. Rev. 2007, 36, 1581.
  • [8] 8Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
  • [9] 9Basavaiah, D.; Roy, S.; Das, U. Tetrahedron, 2010, 66, 5612.
  • [10] 10Basavaiah, D.; Sreenivasulu, B.; Rao, A. J. J. Org. Chem. 2003, 68, 5983.
  • [11] 11Basavaiah, D.; Rao, A. J. Chem. Commun. 2003, 604.
  • [12] 12Basavaiah, D.; Sharada, D. S.; Kumaragurubaran,N.; Reddy, R. M. J. Org. Chem. 2002, 67, 7135.
  • [13] 13Basavaiah, D.; Kumaragurubaran, N.; Sharada, D. S. Tetrahedron Lett. 2001, 42, 85.
  • [14] 14Basavaiah, D.; Gowriswari,V. V. L.; Bharathi, T. K. Tetrahedron Lett. 1987, 28, 4591.
  • [15] 15Basavaiah, D.; Gowriswari, V. V. L. Tetrahedron Lett. 1986, 27, 2031.
  • [16] 16Basavaiah, D.; Badsara, S. S.; Sahu, B. C. Chem. Eur. J. 2013, 19, 2961.
  • [17] 17Basavaiah, D.; Devendar, B.; Aravindu, K.; Veerendhar, A. Chem. Eur. J. 2010, 16, 2031.
  • [18] 18Basavaiah, D.; Devendar, B.; Lenin, D. V.; Satyanarayana, T. Synlett 2009, 411.
  • [19] 19Basavaiah, D.; Roy, S. Org. Lett. 2008, 10, 18
  • [20] 20Basavaiah, D.; Reddy, K. R.; Kumaragurubaran, N. Nature Protocols 2007, 2, 2665.
  • [21] 21Basavaiah, D.; Satyanarayana, T. Chem. Commun. 2004, 32.
Como citar:

Basavaiah, D.; "The Baylis-Hillman reaction: Our vision and experience", p. 327 . In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 2318-4043, DOI 10.5151/chempro-15bmos-13-BASAVAIAH_ABSTRACT_DB-15th_BMOS

últimos 30 dias | último ano | desde a publicação


downloads


visualizações


indexações