C-C Bond Formation via<i>N</i>-Phosphoryliminium Ions

A first successful synthesis of 2-(het)aryl-N-phosphorylpyrrolidines is reported starting from readily available N-(4,4-diethoxybutyl)amides of P(V) acids. A range of phenols and hydroxyl-substituted O-heterocycles may be employed into the reaction furnishing N-phosphorylated 2-(het)arylpyrrolidines with up to 90 % yield. The developed method permits a presence of sensitive to phosphorylation hydroxy groups and provides the easy and regioselective entry to target compounds. Pyrrolidine core is widespread in natural products [1,2] and synthetic drugs. [3] Phosphorus-containing pyrrolidine derivatives are of a special interest due to their various biological [4-8] and catalytic [9,10] properties. Among them, (pyrrolidin-1-yl) phosphoramidates are proposed for hepatitis C, [11] malaria and tuberculosis [12] treatment, possess anti-HIV [13-16] and antitumor [17,18] activity. Additionally, they employed as chiral ligands in various asymmetric reactions. Examples are metal-catalyzed stereoselective reduction of ketones, [19,20] ketimines [21] and alkenes, [22-24] various cycloadditions, [25-29] addition of boronic acids [30] and organotrifluoroborates [31] to alkenes, asymmetric ruthenium-catalyzed metallo-ene reaction [32] and Suzuki-Miyaura coupling. [33]

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2‐(Het)aryl‐N‐phosphorylpyrrolidines via Cyclization of Phosphorus Acid Amides: A Regioselective Approach

Smolobochkin

Турманов

Abdullaeva

et al. 2020

ChemistrySelect

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Diastereoselective Construction of the 6-Oxa-2-azabicyclo[3.2.1]octane Scaffold from Chiral α-Hydroxyaldehyde Derivatives by the Aza-Prins Reaction

et al. 2017

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(R)-2,3-Di-O-benzylglyceraldehyde and N-tosyl homoallylamine undergo aza-Prins cyclization to afford (1R,5S,7S)-7-[(benzyloxy)methyl]-2-tosyl-6-oxa-2-azabicyclo[3.2.1]octane in a highly diastereoselective manner through an unexpected intramolecular nucleophilic attack. Our work has opened a new route toward the asymmetric synthesis of 7-(alkyl or aryl)-6-oxa-2-azabicyclo[3.2.1]octane derivatives from chiral α-hydroxyaldehyde derivatives in one step.

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C-C Bond Formation viaN-Phosphoryliminium Ions

Cited by 2 publications

References 8 publications

2‐(Het)aryl‐N‐phosphorylpyrrolidines via Cyclization of Phosphorus Acid Amides: A Regioselective Approach

2‐(Het)aryl‐N‐phosphorylpyrrolidines via Cyclization of Phosphorus Acid Amides: A Regioselective Approach

Diastereoselective Construction of the 6-Oxa-2-azabicyclo[3.2.1]octane Scaffold from Chiral α-Hydroxyaldehyde Derivatives by the Aza-Prins Reaction

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