AI Article Synopsis

  • A new method using NaI as a catalyst was developed for synthesizing 1-bromo-1-nitroalkan-2-ols through a reaction between bromonitromethane and various aldehydes.
  • The synthesis was conducted under mild conditions, making it an efficient process.
  • The successful reaction with chiral N,N-dibenzyl alaninal produced a specific enantiopure compound, which was confirmed by X-ray analysis.

Article Abstract

[Structure: see text] A catalytic NaI-mediated novel synthesis of 1-bromo-1-nitroalkan-2-ols was carried out by reaction of bromonitromethane with a variety of aldehydes, under very mild conditions. When the reaction was performed with chiral N,N-dibenzyl alaninal, the corresponding enantiopure (1S,2S,3S)-3-dibenzylamino-1-bromo-1-nitrobutan-2-ol was obtained with good stereoselectivity. The structure of this enantiopure bromohydrin was established by X-ray analysis.

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http://dx.doi.org/10.1021/ol062451fDOI Listing

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