The addition of the Np-tolylsulfinyl benzyl idenesimine (R)-2a

July 26, 2024

• Title:       

  The addition of the Np-tolylsulfinyl benzyl idenesimine (R)-2a

• Image Source:

  Chiral monofluorobenzyl carbanions: Synthesis of enantiopure β-fluorinated β-phenylethylamines

• Mark:

  Table 1

• Associated context:

  The addition of the Np-tolylsulfinyl benzyl idenesimine (R)-2a provided a 40:60 mixture of anti-7'a/syn- 8'a in rather low yield (Table 1, entry 1). However, the addition of the imine of the opposite configuration,(S)-2a, afforded the 2-fluoro-2-phenethylamine anti-7a (differing from anti-7'a in the configuration at the sulfinamide sulfur atom)in 81% isolated yield and with almost complete dia- stereoselectivity (entry 2).