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Design of Catalysts for Asymmetric Organic Reactions Through Density Functional Calculations

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Kinetics and Dynamics

Part of the book series: Challenges and Advances in Computational Chemistry and Physics ((COCH,volume 12))

Abstract

The current decade being a golden era in the history of organocatalysis, designing new organocatalysts for synthetically valuable reactions is of high importance. A fine blend of theoretical techniques and knowledge gathered from the experimental observations can help one design highly selective organocatalysts. The present chapter summarizes our efforts in designing organocatalysts for two synthetically important reactions; namely, the aldol reaction and sulfur ylide mediated ring formation reactions. In order to identify the crucial elements that affect the stereoselection process, detailed mechanistic studies are performed initially. Thus, factors controlling the vital energy differences between the diastereomeric transition states are identified and rationalized. Later on, insights from these model studies are utilized toward designing the new catalyst framework. In the last stage, the catalytic efficiency with the designed catalysts is evaluated for selected reactions. Conformationally constrained catalysts designed in this manner are predicted to be more effective with improved selectivities in comparison to the experimentally employed analogues.

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Acknowledgements

Generous computing facilities from IITB computer centre and senior research scholarship from CSIR New Delhi (Shinisha C. B. and Deepa Janardanan) are gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400076, India

    C. B. Shinisha, Deepa Janardanan & Raghavan B. Sunoj

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  1. C. B. Shinisha
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  2. Deepa Janardanan
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  3. Raghavan B. Sunoj
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Editors and Affiliations

  1. Inst. Applied Radiation Chemistry, Dept. Chemistry, Technical University of Lodz, Zeromskiego 116, Lodz, 90-924, Poland

    Piotr Paneth

  2. Inst. Applied Radiation Chemistry, Dept. Chemistry, Technical University of Lodz, Zeromskiego 116, Lodz, 90-924, Poland

    Agnieszka Dybala-Defratyka

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Shinisha, C.B., Janardanan, D., Sunoj, R.B. (2010). Design of Catalysts for Asymmetric Organic Reactions Through Density Functional Calculations. In: Paneth, P., Dybala-Defratyka, A. (eds) Kinetics and Dynamics. Challenges and Advances in Computational Chemistry and Physics, vol 12. Springer, Dordrecht. https://doi.org/10.1007/978-90-481-3034-4_4

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