0000000000179536
AUTHOR
Ana Bartolome
showing 4 related works from this author
Enantioselective synthesis of fluorinated alpha-amino acids and derivatives in combination with ring-closing metathesis: intramolecular pi-stacking i…
2001
[reaction: see text]. Hydride reduction of C=N bonds stereocontrolled by intramolecular pi-stacking interactions of 1-naphthylsulfinyl and N-aryl groups, nonoxidative Pummerer rearrangement, and ring-closing metathesis are efficiently combined in a highly stereoselective entry to enantiomerically pure cyclic and acyclic fluorinated beta-amino alcohols and alpha-amino acid derivatives, respectively.
Novel Approach for Asymmetric Synthesis of Fluorinated β-Amino Sulfones and Allylic Amines
2003
[reaction: see text] Enantiomerically pure gamma-fluoroalkyl beta-amino sulfones are readily synthesized in three steps starting from fluorinated imidoyl chlorides and arylmethyl sulfones. A complementary two-step sequence starting from chiral fluorinated beta-amino sulfoxides has also been developed. To illustrate the application of this procedure, a new method for the synthesis of alpha-fluoroalkyl allylic amines in optically pure form involving a Julia methylenation-desulfonylation reaction is presented.
Diastereoselective synthesis of fluorinated, seven-membered beta-amino acid derivatives via ring-closing metathesis.
2003
[reaction: see text] Cis and trans seven-membered gamma,gamma-difluorinated beta-amino acid derivatives (III) have been prepared with a sequence that starts with imidoyl halides (I), which are condensed with suitable ester enolates to give intermediates (II). These, in turn, can be cyclized by means of a ring-closing olefin metathesis reaction and the product stereoselectively reduced to yield compounds (III) in good overall yields.
Asymmetric synthesis of fluorinated cyclic beta-amino acid derivatives through cross metathesis.
2006
The asymmetric synthesis of several fluorinated cis-2-aminocycloalkane carboxylic acids (cis-2-ACACs) with a cross metathesis (CM) reaction as the key step has been carried out, constituting the first time a metathesis protocol has been undertaken with fluorinated imidoyl chlorides. Subsequent chemoselective hydrogenation of the olefin moiety, Dieckmann condensation, and stereoselective reduction of the iminic double bond afforded the corresponding beta-amino esters with several ring sizes. The asymmetric version of the process was achieved by using (-)-8-phenylmenthol as a chiral auxiliary.