Enantioselective synthesis of α-halo-α-alkylmalonates via phase-transfer catalytic α-alkylation

Org Biomol Chem. 2014 Mar 7;12(9):1510-7. doi: 10.1039/c3ob42107d.

Abstract

A new enantioselective synthetic method for α-halo-α-alkylmalonates is reported. α-Alkylation of diphenylmethyl tert-butyl α-halomalonates under phase-transfer catalytic conditions (solid KOH, toluene, -40 °C) in the presence of (S,S)-3,4,5-trifluorophenyl-NAS bromide (5 mol%) afforded diphenylmethyl tert-butyl α-halo-α-alkylmalonates in very high chemical yields (up to 99%) and optical yields (up to 93% ee).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Catalysis
  • Malonates / chemical synthesis*
  • Malonates / chemistry
  • Molecular Structure
  • Phase Transition
  • Stereoisomerism

Substances

  • Malonates