Multi-component reactions of 2-isopropylidene-aziridines: application to the synthesis of enantiopure neopentylamines

JF Hayes, M Shipman, Alexandra Martha Zoya Slawin, H Twin

Research output: Other contribution

17 Citations (Scopus)

Abstract

Neopentylamines {(1S,1'S)-7a,b} are made from (S)-2isopropylidene-1-(1-phenylethyl)aziridine (4) in 73% and 56% yields respectively, and as single diastereomers, using a multi-component reaction (M-CR). The structure of (1S,1'S)-7a is confirmed by X-Ray crystallography. Cleavage of the chiral control element {(S)-PhMeCH} from 7a yields neopentyl type amine (8(.)HCl) (greater than or equal to95%ee). Further experiments reveal the scope and limitations of this M-CR.

Original languageEnglish
Volume58
Publication statusPublished - 22 Nov 2002

Keywords

  • amine
  • aziridine
  • stereocontrol
  • RING-OPENING REACTIONS
  • 2-METHYLENEAZIRIDINES
  • BOND

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