A New Approach to the Enantioseparation of Betti Bases

Al’fonsov, V. A.; Metlushka, Kirill E.; McKenna, Charles E.; Kashemirov, B. A.; Kataeva, О. N.; Zheltukhin, V. F.; Sadkova, D. N.; Dobrynin, A. B.

doi:10.1055/s-2007-967941

Cited by 22 publications

(12 citation statements)

References 5 publications

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“…[34] Compound 4 a is a polymorph of a previously reported structure (VEYSIC) with a P2 1 space group. [35] The conformations of both the structures are similar with a root-meansquare deviation of 0.3 . The molecular interactions are described in Table 3.…”

Section: Resultsmentioning

confidence: 84%

Selective Synthesis and Structural Confirmation of 1,3‐Oxazines and Schiff Bases with Controllable Substitution Patterns

et al. 2012

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Selective synthesis of 2,4‐diaryl‐2,3‐dihydro‐3H‐naphtho[1,2‐e]‐1,3‐oxazines and Schiff bases ((E)‐[1‐arylmethyl(benzylideneamino)]naphth‐2‐ols) that contain two identical or two different aryl substituents was achieved through one‐pot synthesis with ammonium acetate. From the proposed mechanism the dual role of ammonium acetate was identified. The synthesized products were characterized by 1H and 13C NMR spectroscopy, as well as FTIR and mass spectrometry. Crystal structures of the 1,3‐oxazines and Schiff base derivatives were examined. A notable feature is the conspicuous absence of strong donors (NH/OH) in any intermolecular hydrogen‐bonding scheme. Instead, packing is characterized by weak intermolecular CH⋅⋅⋅O, CH⋅⋅⋅π and CCl⋅⋅⋅π interactions, which lead to dimeric and zig‐zag one‐dimensional molecular patterns. The oxazine moiety of the tricyclic ring system predominantly adopts a half‐chair conformation. The present Mannich procedure is an environmentally benign and cost‐effective method for the preparation of industrially and pharmaceutically useful heterocyclic scaffolds.

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Section: Resultsmentioning

confidence: 84%

Selective Synthesis and Structural Confirmation of 1,3‐Oxazines and Schiff Bases with Controllable Substitution Patterns

et al. 2012

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“…[7] In the present work, we demonstrate the potential of these readily available Betti adducts as chiral inductors for the synthesis of enantiopure a-aminophosphonates.…”

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confidence: 72%

1‐(α‐Aminobenzyl)‐2‐naphthol: A New Chiral Auxiliary for the Synthesis of Enantiopure α‐Aminophosphonic Acids

Metlushka

Kashemirov

Zheltukhin

et al. 2009

Chemistry A European J

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A new diastereoselective synthesis of alpha-aminophosphonates has been developed, based on the reaction, in the presence of trifluoroacetic acid, of trialkyl phosphites with chiral imines derived from (R)- or (S)-1-(alpha-aminobenzyl)-2-naphthol. The reaction proceeds at room temperature in toluene with high diastereoselectivity. The major diastereomer can be separated by crystallization from an appropriate solvent. The relative configuration of both chiral centers of the major diastereomer was determined by single-crystal X-ray structure analysis. The desired alpha-aminophosphonic acids can be obtained in enantiopure form by treatment of the corresponding diastereomers with HCl.

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“…The products of this reaction were (S)-3a tartrate, the acetal of benzaldehyde and tartaric acid, and (þ)-2a, which were easily separated by crystallization (Scheme 1). 22 Harrison et al recently reported the syntheses of 6-bromosubstituted aminonaphthol derivatives (9aen) from 6-bromo-2-naphthol (7), methanolic ammonia and the corresponding aromatic aldehyde. The naphthoxazine intermediates 8aen were hydrolysed with hydrochloric acid to yield the desired aminonaphthol derivatives 9aen (Scheme 3).…”

Section: Syntheses With Ammonia As N Sourcementioning

confidence: 99%

Syntheses, transformations and applications of aminonaphthol derivatives prepared via modified Mannich reactions

Szatmári

Fülöp

2013

Tetrahedron

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A New Approach to the Enantioseparation of Betti Bases

Cited by 22 publications

References 5 publications

Selective Synthesis and Structural Confirmation of 1,3‐Oxazines and Schiff Bases with Controllable Substitution Patterns

Selective Synthesis and Structural Confirmation of 1,3‐Oxazines and Schiff Bases with Controllable Substitution Patterns

1‐(α‐Aminobenzyl)‐2‐naphthol: A New Chiral Auxiliary for the Synthesis of Enantiopure α‐Aminophosphonic Acids

Syntheses, transformations and applications of aminonaphthol derivatives prepared via modified Mannich reactions

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