175416-53-2Relevant academic research and scientific papers
An efficient entry to optically active anti- and syn-β-amino-α- trifluoromethyl alcohols
Fustero, Santos,Albert, Laia,Acena, Jose Luis,Sanz-Cervera, Juan F.,Asensio, Amparo
, p. 605 - 608 (2008/09/16)
The reaction of chiral 5,6-dihydro-2H-1,4-oxazin-2-ones with TMSCF 3 in the presence of a suitable activator leads to trifluoromethyl lactols, which can be selectively reduced to anti-β-amino-α- trifluoromethyl alcohols. The corresponding syn d
Oxidative rearrangement of 2-substituted oxazolines. A novel entry to 5,6-dihydro-2H-1,4-oxazin-2-ones and morpholin-2-ones
Shafer,Molinski
, p. 2044 - 2050 (2007/10/03)
A novel synthesis of 5,6-dihydro-2H-1,4-oxazin-2-ones by SeO2-promoted oxidative rearrangement of 2-alkyl- and 2-(arylmethyl)oxazolines is described. Yields are good to excellent (up to 94%) with the highest yields obtained for 2-arylmethyl- and 2-neopentyl-substituted oxazolines. This reaction provides convenient access to novel 5-aryl-substituted dihydrooxazinones in high yield. The latter compounds are important 'chiral glycine' synthons for asymmetric synthesis of α-amino acids. Since oxazolines are readily derived from carboxylic acids or their equivalents, this oxidative rearrangement constitutes an entry to synthesis of α-amino acids from carboxylic acids. A mechanism is proposed to account for the rearrangement involving a 'nitrilium to acylium' 1,2-migration.
