ChemInform Abstract: Synthetic Utility of Sugar‐Derived Cyclic Nitrones: A Diastereoselective Synthesis of Linear 4‐Azatriquinanes.

Bandaru, Anandaraju; Kaliappan, Krishna P.

doi:10.1002/chin.201242118

Cited by 1 publication

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The addition of vinylmagnesium bromide to polyhydroxylated cyclic nitrones was the starting point for the synthesis of variety of alkaloids such as 4-azatriquinanes, [39] DMDP, [40] hyacinthacine A 2 [41]and (+)-lentiginosine, [42]and other substituted polyhydroxylated pyrrolidines with biological activity as chaperones for Gaucher disease. [43] In general, the addition took place with excellent trans-selectivity with respect to the substituent placed at α-position of the nitrone carbon to form the corresponding N-hydroxypyrrolidines 26a-32a (Scheme 7).…”

Section: Methodsmentioning

confidence: 99%

Recent Advances in the Preparation of Enantiomerically Pure Hydroxylamines from Nitrones

Matute¹,

García‐Viñuales²,

Hayes³

et al. 2016

COS

View full text Add to dashboard Cite

This review covers the recent advances in the synthesis of enantiomerically pure hydroxylamines employing nitrones as starting materials. Nucleophilic additions of organometallic reagents to nitrones are the most common way for introducing a hydroxyamino group into carbon skeletons with the concomitant formation of a new carbon-carbon bond. Addition of carbanions derived from enolates, cyanide or fluorinated derivatives allow the preparation of complex structures. Radical additions and, in particular samarium diiodide-mediated reductive coupling of nitrones with carbonyl compounds and α,β-unsaturated esters have also been considered. All these approaches provide efficient methods of preparation of enantiomerically pure hydroxylamienes that are valuable synthetic intermediates. KeywordsHydroxylamines; Nitrones; Organometallics; Mannich; Reductive coupling 2 Graphical Abstract 3

show abstract

Section: Methodsmentioning

confidence: 99%

Recent Advances in the Preparation of Enantiomerically Pure Hydroxylamines from Nitrones

Matute¹,

García‐Viñuales²,

Hayes³

et al. 2016

COS

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: Synthetic Utility of Sugar‐Derived Cyclic Nitrones: A Diastereoselective Synthesis of Linear 4‐Azatriquinanes.

Abstract: A convenient 3‐step sequence is used to prepare the precursors from the corresponding nitrones.

Cited by 1 publication

References 0 publications

Recent Advances in the Preparation of Enantiomerically Pure Hydroxylamines from Nitrones

Recent Advances in the Preparation of Enantiomerically Pure Hydroxylamines from Nitrones

Contact Info

Product

Resources

About