The Betti base: absolute configuration and routes to a family of related chiral nonracemic bases

Syntheses and Transformations of 1-(α-Aminobenzyl)-2-Naphthol Derivatives

“…and its absolute configuration was found to be (S) (determined by X-ray diffraction analysis of its hydrobromide salt, 3a.HBr). 30 The N,N-dimethylamino derivative of 3a was resolved in a similar manner. The diastereomeric salts obtained from the racemate and (2R,3R)-tartaric acid were separated by fractional crystallization from acetone.…”

“…The diastereomeric salts obtained from the racemate and (2R,3R)-tartaric acid were separated by fractional crystallization from acetone. 30 The N-butyl derivative of 3a could be resolved by using an equivalent amount of (2R,3R)-tartaric acid in acetone. …”

Bioactivity of a Family of Chiral Nonracemic Aminobenzylnaphthols towards Candida albicans

“…The structures of the two different stereoisomers (R,S)-7 and (S,S)-7 were optimized with an HF-calculation (Spartan program), with the further constrain of a hydrogen bond between the naphthol hydrogen atom and the nitrogen atom, fixed at the average value of 1.85 Å, as occurred in every other aminobenzylnaphthols [14,17]. Within this constrain, the calculation shows that the exocyclic methylene group points towards the phenyl moiety in the case of the (S,S)-aminobenzylnaphthol 7, whereas the same group points towards free space in the case of the (R,S)-counterpart ( Figure 5).…”

“…Previously, some papers [14][15][16][17][18][19] reported the Betti reaction as a route for the asymmetric synthesis of chiral nonracemic amino benzylnaphthols. This procedure is a straightforward condensation of 2-naphthol, aryl aldehydes and suitable chiral nonracemic amines (Schemes 1 and 2) to yield more complex molecular structures.…”

Electron ionization mass spectra of naphthoxazine, naphthpyrrolo-oxazinone and naphthoxazinobenzoxazine derivatives

“…(1-α-aminobenzyl)-2-naphthols, are useful synthons in the ring closure reactions. [2][3][4] They and their analogues commonly contain stereogenic centers and therefore regioselective and diastereoselective syntheses using Betti base synthons is gaining popularity. For example the ligands corresponding to the structure of N,N-dialkyl Betti base are becoming important in asymmetric syntheses catalyzed by metallic ions.…”