Current trends and advancements in Ferrier and Petasis-Ferrier rearrangement

Jose, Vidya; Diana, Elizabeth J.; Kanchana, U.S.; Mathew, Thomas

doi:10.1016/j.jorganchem.2023.122691

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2024

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Cited by 4 publications

(2 citation statements)

References 36 publications

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“…11 The Ferrier rearrangement is a nucleophilic substitution reaction in glycals with a migration of a double bond to the 2,3-position in the presence of an activator. 11–14 In this scenario, these glycals predominantly yielded allylic pyranoses rather than 2-deoxy sugars. These allylic pyranoses can be converted into deoxy sugars upon reduction.…”

Section: Introductionmentioning

confidence: 99%

TFA-induced conversion of glycals to 2-deoxy-sugars and their utility in synthesizing 2-deoxy-glycosyl esters

Tiwari,

Pandey,

Hussain

2024

New J. Chem.

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Section: Introductionmentioning

confidence: 99%

TFA-induced conversion of glycals to 2-deoxy-sugars and their utility in synthesizing 2-deoxy-glycosyl esters

Tiwari,

Pandey,

Hussain

2024

New J. Chem.

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“…Herein we disclose a novel strategy by reaction of 3,4-dihydro-2 H -pyran derivatives with potassium alkenyltrifluoroborates achieving their α-alkenylation (Scheme 1C). This protocol features mild reaction conditions, readily available starting materials, broad substrate scope and diverse valuable products, and the substrates of glycals can be adapted through a Ferrier-type 12 alkenylation process to obtain the corresponding functionalized sugars.…”

mentioning

confidence: 99%

Brønsted acid-mediated selective α-alkenylation of 3,4-dihydro-2H-pyrans

Chen,

Li,

Liao

et al. 2024

Org. Chem. Front.

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Expanding 1‐Aminosugar Synthesis through Activated Glycals’ Reactivity

Li,

Lemouton,

Al Ayi

et al. 2024

Eur J Org Chem

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Glycal family offers an interesting platform whose reactivity let the possibility to reach diverse glycoanalogues. In particular, the Ferrier rearrangement allows the introduction of diverse nucleophiles on the anomeric position but stays limited with regard to the nitrogen‐containing nucleophiles, which can be possibly used with success. Herein, we utilize peracetylated C2‐substituted glycal substrates to achieve Ferrier‐type 1‐aminoglycoside compounds under activator‐free conditions, resulting in moderate to good yields and good to excellent β‐selectivity. Various secondary amines have been successfully employed. We explored the influence of C2‐substitution (electron‐withdrawing character) and glycal configuration, synthesizing 20 different 1‐aminoglycosides through this method.

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Current trends and advancements in Ferrier and Petasis-Ferrier rearrangement

Cited by 4 publications

References 36 publications

TFA-induced conversion of glycals to 2-deoxy-sugars and their utility in synthesizing 2-deoxy-glycosyl esters

TFA-induced conversion of glycals to 2-deoxy-sugars and their utility in synthesizing 2-deoxy-glycosyl esters

Brønsted acid-mediated selective α-alkenylation of 3,4-dihydro-2H-pyrans

Expanding 1‐Aminosugar Synthesis through Activated Glycals’ Reactivity

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