0000000000179538

AUTHOR

Juan García Soler

showing 3 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.

Molecular StructureChemistryHydrideStereochemistryPummerer rearrangementOrganic ChemistryStackingEnantioselective synthesisStereoisomerismFluorineMetathesisBiochemistryRing-closing metathesisIntramolecular forcePhysical and Theoretical ChemistryAmino AcidsAcyclic diene metathesisOrganic letters
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Synthesis of nonracemic α-trifluoromethyl α-amino acids from sulfinimines of trifluoropyruvate

2001

We describe a novel and useful method for the synthesis of nonracemic α-trifluoromethyl α-amino acids (α-Tfm-AAs). Key building blocks are the sulfinimines (S)-1a and (S)-1b, prepared by Staudinger reaction from trifluoropyruvate esters and the chiral N-sulfinyl iminophosphorane (S)-8, which were treated with benzyl, allyl, and alkylmagnesium halides. The resulting diastereomeric N-sulfinyl α-Tfm α-amino esters, 12 and 13, were produced with moderate to good stereoselectivity and yields. When alkyl Grignard reagents were used, stereocontrol became progressively higher with increasing steric bulk, while reversed, though poor, stereocontrol was achieved with benzyl/allyl Grignard reagents. An…

chemistry.chemical_classificationSteric effectsTrifluoromethylChemistryStereochemistryOrganic ChemistryEnantioselective synthesisDiastereomerchemistry.chemical_compoundReagentStereoselectivityStaudinger reactionPhysical and Theoretical ChemistryAlkyl
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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.

Allylic rearrangementHydrocarbons FluorinatedChemistryorganic chemicalsOrganic ChemistryEnantioselective synthesisStereoisomerismGeneral MedicineCombinatorial chemistryBiochemistryAllyl CompoundsOrganic chemistrySulfonesAminesPhysical and Theoretical ChemistryOrganic Letters
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