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Enantioselective Michael addition of malonic esters to benzalacetophenone by using chiral phase transfer catalysts derived from proline-mandelic acid/tartaric acid

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Abstract

Herein, we have explored the enantioselective Michael addition of various malonate esters to benzalacetophenone by successful utilization of chiral phase transfer catalysts derived from proline, mandelic acid and tartaric acid under mild phase transfer conditions. The obtained results signify that these chiral phase transfer catalysts are efficacious towards enantioselective Michael addition as the use of it resulted in good enantioselectivity and appreciable chemical yields.

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SYNOPSIS Highly enantioselective Michael addition of dialkyl malonates to benzalacetophenone has been established under mild phase transfer conditions, by successful utilization of chiral phase transfer catalysts derived from proline, mandelic acid and tartaric acid (I–VI) with appreciable chemical yields.

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Acknowledgements

The authors are thankful to the M/S Lupin Limited and the authorities of Manipal Academy of Higher Education for the research program. We also acknowledge the valuable guidance, support and suggestions from Dr. P. R. Upadhaya and Dr. Vijaya Desai.

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  1. Lupin Limited, 46 & 47A, Village Nande, Taluka Mulshi, Pune, Maharashtra, 412 115, India

    Deepak P Mahajan, Himanshu M Godbole & Girij P Singh

  2. Manipal Academy of Higher Education, Manipal, Karnataka, 576 104, India

    Gautham G Shenoy

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  1. Deepak P Mahajan
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Correspondence to Deepak P Mahajan.

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Mahajan, D.P., Godbole, H.M., Singh, G.P. et al. Enantioselective Michael addition of malonic esters to benzalacetophenone by using chiral phase transfer catalysts derived from proline-mandelic acid/tartaric acid. J Chem Sci 131, 67 (2019). https://doi.org/10.1007/s12039-019-1642-5

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