Journal of Chemical Sciences

, Volume 129, Issue 10, pp 1603–1610 | Cite as

Enantioselective aminocatalysis: Michael addition of unactivated ketones to nitroolefins catalyzed by D-fructose derived monofunctional primary amine

  • Khiangte Vanlaldinpuia
  • Porag Bora
  • Grace Basumatary
  • Rahul Mohanta
  • Ghanashyam Bez
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Abstract

Organocatalytic asymmetric Michael addition is considered among the most extensively studied, yet challenging stereoselective reactions due to the fact that the electrophilic prochiral carbon in Michael acceptor lies away from stereodirecting groups of the catalyst. Although there is a report on stereoselective organocatalysis in Michael addition employing monofunctional secondary amine, the use of monofunctional primary amine for the said reaction is not reported till date. In fact, no monofunctional aminocatalyst is reported yet for the synthesis \(\upgamma \)-nitro carbonyl compounds. Here we report our preliminary results on the enantioselective Michael addition of different ketones to nitro olefins catalysed by monofunctional primary amine (1) derived from d-fructose.

Graphical Abstract

Monofunctional primary amine is used for the first time as catalyst for stereoselective Michael addition reaction of different ketones to nitro olefins to synthesize \(\upgamma \)-nitro carbonyl compounds.

Keywords

Stereoselective aminocatalysis monofunctional amine d-fructose Michael addition nitroalkene 

Notes

Acknowledgements

Authors acknowledge the Council of Scientific and Industrial Research (CSIR), New Delhi, India for financial support (Scheme No. 1 (1992)/05/EMR-II). The analytical service provided by Sophisticated Analytical Instrument Facility, North Eastern Hill University, Shillong is gratefully acknowledged.

Supplementary material

12039_2017_1371_MOESM1_ESM.pdf (12.2 mb)
Supplementary material 1 (pdf 12500 KB)

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Copyright information

© Indian Academy of Sciences 2017

Authors and Affiliations

  • Khiangte Vanlaldinpuia
    • 1
    • 2
  • Porag Bora
    • 1
  • Grace Basumatary
    • 1
  • Rahul Mohanta
    • 1
  • Ghanashyam Bez
    • 1
  1. 1.Department of ChemistryNorth Eastern Hill UniversityShillongIndia
  2. 2.Department of ChemistryPacchunga University CollegeAizawlIndia

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