Production of enantiopure β-amino-γ-hydroxyesters from benzoic acid by a selective formal aminohydroxylation

Pazos, Mariana; Gonzalez, Bruno J.; Seoane, Gustavo; Suescun, Leopoldo

doi:10.1016/j.tetlet.2017.04.048

Cited by 10 publications

(5 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In fact, using an excess NBS this compound was converted at first into the chiral tricyclic imidazolidine 130, whereas a further bromination at the nitrogen atom gave the intermediate 131. The subsequent elimination reaction led in moderate yield but with total stereoselectivity to the tricyclic compound 132, containing a 4,5-dihydroimidazole moiety, that was eventually converted into (-)-γ-licorane, 133 [100], a degradation product of several members of the caranine family of alkaloids (Scheme 33) [101].…”

Section: 5-dihydroimidazolesmentioning

confidence: 99%

Chiral non Aromatic Nitrogen-Heterocycles by Asymmetric Intramolecular Haloamination and Haloamidation

Orena*

2024

Preprint

View full text Add to dashboard Cite

This review deals with the functionalization of double bonds carried out in the presence of a chiral catalyst exploiting the intramolecular attack to haliranium ions by nucleophilic nitrogen of amides or carbamates prepared from achiral aminoalkenes, and the C-N bonds formation leads to highly enantioenriched non-aromatic heterocycles. A range of protocols are reported, emphasizing the synthesis of many natural and biologically active products of pharmacological interest prepared according to this methodology.

show abstract

Section: 5-dihydroimidazolesmentioning

confidence: 99%

Chiral non Aromatic Nitrogen-Heterocycles by Asymmetric Intramolecular Haloamination and Haloamidation

Orena*

2024

Preprint

View full text Add to dashboard Cite

show abstract

“…Since the dienic system in 49 does not present any substituent to allow for the differentiation of both olefins, selective functionalization is difficult, mainly with N ‐containing reagents. We decided to probe the reactivity of this system and found a novel regio‐ and stereoselective protocol for a formal aminohydroxylation of the diene in 49 [77] . The sequence started with the protection of the diol functionality and tosylamide formation to give 50 , which was submitted to a selective halonium‐induced β‐lactamization to afford a separable mixture of bromo lactams 51 in a 91 : 9 ratio (Scheme 17).…”

Section: Synthesis Of Building Blocksmentioning

confidence: 99%

“…We decided to probe the reactivity of this system and found a novel regio-and stereoselective protocol for a formal aminohydroxylation of the diene in 49. [77] The sequence started with the protection of the diol functionality and tosylamide formation to give 50, which was submitted to a selective halonium-induced β-lactamization to afford a separable mixture of bromo lactams 51 in a 91 : 9 ratio (Scheme 17). The major β-lactam 51 a was opened with different nucleophiles using KCN as catalyst.…”

Section: Amino Hydroxy Estersmentioning

confidence: 99%

Achievements, Challenges, and Scope of Thirty Years of Work on the Biotransformation of Arenes and Their Synthetic Applications

et al. 2022

Self Cite

View full text Add to dashboard Cite

show abstract

“…Diastereodivergent synthesis of protected β-amino-γ-hydroxy esters from a common bicyclic β-lactam has been achieved by Carrera and co-workers. 58 Starting from benzoic acid and using enzymatic dihydroxylation with the mutant strain Ralstonia eutropha B9, an enantiopure cis-cyclohexadiendiol was obtained. This compound was further transformed into the β-lactam, which by treatment with KCN in methanol gave an aziridine.…”

Section: β-Amino Acidsmentioning

confidence: 99%

Stereodivergent routes in organic synthesis: carbohydrates, amino acids, alkaloids and terpenes

et al. 2020

View full text Add to dashboard Cite

The natural occurrence of enantio-and diastereomers is often encountered. In addition, the synthesis of these stereoisomers is important for structure determination and for the study of structure-activity-relationships. Stereodivergent routes simplify the access to these molecules starting from a common material. This review is focused on the synthesis of carbohydrates, amino acids, alkaloids and terpenes using this efficient strategy. In the case of carbohydrates, such as monosaccharides, carbasugars, aminosugars and azasugars, carbohydrates are usually employed as common starting materials. As a very common strategy, configurations of hydroxy groups are inverted by S N 2 methods playing with protection and deprotection processes. For the synthesis of acyclic α-AAs diastereoselective methods using mainly Garner's aldehyde have been described. Diastereodivergent routes allowed the synthesis of β-hydroxy-and β-amino-α-amino acids, as well as of β-and γ-amino acids. Heterocyclic and cyclic amino phosphonic acids were synthesized using diastereodivergent routes. Alkaloids containing five-and six-membered saturated azaheterocycles needed multistep stereodivergent routes as well as other alkaloids, such as enantiomers of balanol, vincamine, anatoxin and codeine and diastereomeric isochaetominines C and galanthamines. In the terpene field, sesquiterpenes β-santalene, αcurcumene and α-cuparenone and the diterpene scopadulcic acid A were synthesized using enantiodivergent routes. ____________________________________________________________________________

show abstract

Production of enantiopure β-amino-γ-hydroxyesters from benzoic acid by a selective formal aminohydroxylation

Cited by 10 publications

References 31 publications

Chiral non Aromatic Nitrogen-Heterocycles by Asymmetric Intramolecular Haloamination and Haloamidation

Chiral non Aromatic Nitrogen-Heterocycles by Asymmetric Intramolecular Haloamination and Haloamidation

Achievements, Challenges, and Scope of Thirty Years of Work on the Biotransformation of Arenes and Their Synthetic Applications

Stereodivergent routes in organic synthesis: carbohydrates, amino acids, alkaloids and terpenes

Contact Info

Product

Resources

About