Abbreviated as DAST. Commonly used as a fluorinating reagent to converts alcohols to the corresponding alkyl fluorides as well as aldehydes and unhindered ketones to geminal difluorides.1,2 Applied as a catalyst for Friedel-Crafts allylation using tertiary cyclopropyl silyl ethers,3 the rearrangement of homoallylic alcohols to unsaturated aldehydes,4 and the fluoro-Pummerer rearrangement of sulfoxides.5 Also employed in the selective monofluorination of sugars,6 conversion of N-protected amino acids to the acyl fluorides,7 gem difluorination of ketopipecolinic acids,8 and stabilization of the epoxide during further manipulations in the synthesis of 26-fluoro-epothilone.9
Reference
1. Eur. J. Org. Chem. 2000, 3177.
2. Tetrahedron Lett. 2003, 44, 6661.
3. Tetrahedron Lett. 2006, 47, 3777.
4. Org. Lett. 2006, 8, 2091.
5. J. Am. Chem. Soc. 1985, 107, 735 (1985)
6. J. Chem. Soc., Perkin 2, 1995, 861.
7. Indian J. Chem. 2000, 39, 384.
8. Tetrahedron Lett. 2004, 45, 1445.
9. Synlett 2004, 693-697.