Zinc mediated allylations of chlorosilanes promoted by ultrasound: synthesis of novel constrained sila amino acids

Org Biomol Chem. 2014 Jun 28;12(24):4093-7. doi: 10.1039/c4ob00294f.

Abstract

A simple, fast and efficient method for allylation and propargylation of chlorosilanes through zinc mediation and ultrasound promotion is reported. As a direct application of the resulting bis-allylsilanes, three novel, constrained sila amino acids are prepared for the first time. The design and synthesis of the constrained sila analogue of GABA (γ-amino butyric acid) is a highlight of this work.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Silanes / chemical synthesis*
  • Silanes / chemistry
  • Silicon / chemistry
  • Ultrasonics / methods*
  • Zinc / chemistry*
  • gamma-Aminobutyric Acid / analogs & derivatives
  • gamma-Aminobutyric Acid / chemical synthesis

Substances

  • Amino Acids
  • Silanes
  • gamma-Aminobutyric Acid
  • Zinc
  • Silicon