Approach to a better understanding and modeling of (S)-dihydrofuran-2-yl, (S)-tetrahydrofuran-2-yl-, and furan-2-yl-β-dialkylaminoethanol ligands for enantioselective alkylation

New class of β-aminoalcohol ligands derived from isosorbide and isomannide: application in hydrogen transfer reduction of prochiral ketones

“…Moreover, it is noteworthy that in our case, the stereochemistry of the chiral center located on the position 2 of the THF ring of a and b series seemed to have no influence on the enantioselectivity of the HTR of ketones, as it has been observed by Paolucci and Rosini for the asymmetric addition of diethylzinc to benzaldehyde 36 with THF ring substituted in position 2 with b-aminoalcohol functionality.…”

“…21 Otherwise, isosorbide and isomannide derivatives were considered as factor Xa inhibitors 22,23 and isommanide pseudopeptides derivatives as serine protease inhibitors. 24 Isosorbide and isomannide were also used in the synthesis of biodegradable polymers, 25e28 amphiphiles, 29 chiral auxiliaries 30e34 or as starting material for catalyst used for enantioselective alkylation 35,36 or in chiral phase transfer catalysis. 37,38 Isomannide has found application as precursor of chiral ionic liquids for chiral discrimination and optical resolution of racemates.…”

Biosourced Ligands from Isosorbide for the Ethylation of Aldehydes or Alkynylation of Imines

“…[7] Twoy ears later,P aolucci and Rosini prepared as eries of di-o rt etrahydrofuran-2-yls and furan-2-yl-dialkylaminoethanols from isosorbide or isomannide. [8] These compounds were used as ligands in the addition of diethylzinc to aldehydes;h owever,t hey did not preserve the structural integrityo ft he 1,4:3,6-dianhydrohexitol skeleton (Scheme 1).…”

Iodoetherification of Isosorbide‐Derived Glycals: Access to a Variety of O‐Alkyl or O‐Aryl Isosorbide Derivatives

“…However acidic conditions promote a rearrange- ment that leads to the corresponding mono protected 2furanyl ethanediol 6 (Scheme 3). [18]…”