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Exo selective enantioselective nitrone cycloadditions.

Mukund P Sibi1, Zhihua Ma, Craig P Jasperse

  • 1Department of Chemistry, North Dakota State University, Fargo, North Dakota 58105, USA. mukund.sibi@ndsu.nodak.edu

Journal of the American Chemical Society
|January 22, 2004
PubMed
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Researchers created a new way to make specific nitrone cycloaddition products. Using pyrazolidinones as templates and copper triflate, they achieved high selectivity and enantioselectivity for exo adducts.

Area of Science:

  • Organic Chemistry
  • Asymmetric Synthesis

Background:

  • Nitrone cycloadditions are important reactions in organic synthesis.
  • Achieving high stereoselectivity, particularly exo selectivity, in these reactions can be challenging.

Purpose of the Study:

  • To develop a novel method for accessing exo adducts with high enantioselectivity in nitrone cycloadditions to enoates.
  • To identify effective templates and reaction conditions for promoting exo selectivity.

Main Methods:

  • Utilized pyrazolidinones as achiral templates in nitrone cycloadditions to enoates.
  • Employed Lewis acids, specifically those forming square planar complexes like copper triflate, to influence stereochemical outcomes.

Main Results:

  • Achieved high exo adduct selectivity, typically greater than 15:1.

Related Experiment Videos

  • Obtained high enantioselectivity, with enantiomeric excess (ee) ranging from 90-98%.

    • Conclusions:

    • Pyrazolidinones are effective achiral templates for high exo selectivity in nitrone cycloadditions.
    • The use of square planar Lewis acids, such as copper triflate, is crucial for achieving high exo selectivity and enantioselectivity.