Differential reactivity of fluorinated homopropargylic amino esters vs gold(I) salts. The role of the nitrogen protecting group

作者：Sanchez Rosello Maria; Miro Javier; del Pozo Carlos^*; Fustero Santos

来源：Journal of Fluorine Chemistry, 2015, 171: 60-66.

DOI：10.1016/j.jfluchem.2014.09.017

• Fluorinated homopropargyl amino esters
• Gold catalysis
• Fluorinated dihydro-quinolines
• Fluorinated oxazines
• Fluorinated alfa-amino acid derivatives

The reaction of several homopropargyl amino esters 4, bearing aromatic substituents and a benzyl group as nitrogen substituents, with gold(I) salts gave rise to fluorinated quinolines 6 in a tandem hydroarylation-isomerization process. On the other hand, homopropargyl amino esters 7 containing a carbamate group underwent the carbonyl addition over the triple bond in the presence of gold(I) salts, rendering fluorinated oxazines 8. The use of chiral sulfoxides allowed us to develop the asymmetric version of this protocol. This two processes complete the differential reactivity showed by these types of susbtrates, depending on the nature of the nitrogen protecting group.

• 出版日期2015-3