6533b827fe1ef96bd1286765
RESEARCH PRODUCT
An efficient entry to optically active anti- and syn-beta-amino-alpha-trifluoromethyl alcohols.
Santos FusteroJosé Luis AceñaLaia AlbertAmparo AsensioJuan F. Sanz-cerverasubject
chemistry.chemical_compoundTrifluoromethylNitrogen atomStereochemistryChemistryLactolOrganic ChemistryImineDiastereomerPhysical and Theoretical ChemistryOptically activeBiochemistrydescription
The reaction of chiral 5,6-dihydro-2H-1,4-oxazin-2-ones with TMSCF3 in the presence of a suitable activator leads to trifluoromethyl lactols, which can be selectively reduced to anti-beta-amino-alpha-trifluoromethyl alcohols. The corresponding syn diastereoisomers are obtained when the starting imines are reduced and the nitrogen atom is conveniently protected. In addition, a novel rearrangement of the CF3 group in the lactol intermediates has been observed. This represents a formal CF3 addition to the imine function in the starting substrates.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2008-01-24 | Organic letters |