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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
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An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
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The chiral α-carbon of the carbonyl compound is the stereocenter of the molecule. As shown in the figure below, when such a carbonyl compound undergoes racemization under an acidic or basic condition, an achiral enol is formed.
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Carbamate-catalyzed enantioselective bromolactamization.

Yi An Cheng1, Wesley Zongrong Yu1, Ying-Yeung Yeung2,3

  • 1Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore).

Angewandte Chemie (International Ed. in English)
|August 29, 2015
PubMed
Summary

Researchers developed a new method for enantioselective bromolactamization using a carbamate catalyst. This efficient process yields enantioenriched bromolactam products with high stereoselectivity.

Keywords:
asymmetric catalysiscyclizationslactamsorganocatalysisreaction mechanisms

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Area of Science:

  • Organic Chemistry
  • Asymmetric Synthesis
  • Catalysis

Background:

  • Bromolactamization is a valuable synthetic transformation for constructing nitrogen-containing heterocycles.
  • Developing efficient and enantioselective methods for bromolactamization remains a key challenge in organic synthesis.
  • Olefinic amides are versatile starting materials for cyclization reactions.

Purpose of the Study:

  • To develop a highly facile, efficient, and enantioselective bromolactamization of olefinic amides.
  • To explore the use of a carbamate catalyst in promoting N-cyclization.
  • To synthesize a diverse range of enantioenriched bromolactam products.

Main Methods:

  • Employing a carbamate catalyst for the bromolactamization reaction.
  • Utilizing ethanol as an additive to facilitate the N-cyclization process.
  • Investigating the scope and limitations of the developed methodology with various olefinic amide substrates.

Main Results:

  • Achieved a highly facile and efficient enantioselective bromolactamization.
  • The carbamate catalyst effectively promoted N-cyclization of the amide substrates.
  • Generated a diverse range of enantioenriched bromolactam products containing up to two stereogenic centers.
  • Demonstrated high levels of enantioselectivity in the synthesized products.

Conclusions:

  • The developed carbamate-catalyzed bromolactamization is a powerful and efficient method for accessing enantioenriched bromolactams.
  • This methodology offers a valuable tool for the synthesis of complex chiral molecules.
  • The reaction proceeds with high stereocontrol, providing access to valuable synthetic intermediates.