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Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

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ABSTRACT

Multicomponent reactions (MCRs) are one of the most important processes for the preparation of highly functionalized organic compounds in modern synthetic chemistry. As shown in this review, they play an important role in organophosphorus chemistry where phosphorus reagents are used as substrates for the synthesis of a wide range of phosphorylated heterocycles. In this article, an overview about multicomponent reactions used for the synthesis of heterocyclic compounds bearing a phosphonate group on the ring is given.

No MeSH data available.


An asymmetric version of the Kabachnik–Fields reaction for the synthesis of α-amino-3-piperidinylphosphonic acids.
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C11: An asymmetric version of the Kabachnik–Fields reaction for the synthesis of α-amino-3-piperidinylphosphonic acids.

Mentions: An asymmetric synthesis of heterocyclic α-aminophosphonates has been reported by Fadel et al. [37]. Their studies showed that the three-component reaction of N-Boc-3-piperidinone (37), (S)-configured amines 39 and triethyl phosphite (38), in the presence of 2 equiv of AcOH and 0.8 equiv of MgSO4 at 50 °C afforded a 60:40 diastereomeric mixture of α-aminophosphonates (R,S)-40 and (S,S)-41 in 75% combined yield. The cleavage of the N-Boc group followed by removal of the benzyl groups and acidic hydrolysis of the resulting (α-amino-3-piperidinyl)phosphonates (R)-42 and (S)-43 led to enantiopure α-amino-3-piperidinylphosphonic acids (R)-44 and (S)-45 in good yields (Scheme 11).


Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates
An asymmetric version of the Kabachnik–Fields reaction for the synthesis of α-amino-3-piperidinylphosphonic acids.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC4979670&req=5

C11: An asymmetric version of the Kabachnik–Fields reaction for the synthesis of α-amino-3-piperidinylphosphonic acids.
Mentions: An asymmetric synthesis of heterocyclic α-aminophosphonates has been reported by Fadel et al. [37]. Their studies showed that the three-component reaction of N-Boc-3-piperidinone (37), (S)-configured amines 39 and triethyl phosphite (38), in the presence of 2 equiv of AcOH and 0.8 equiv of MgSO4 at 50 °C afforded a 60:40 diastereomeric mixture of α-aminophosphonates (R,S)-40 and (S,S)-41 in 75% combined yield. The cleavage of the N-Boc group followed by removal of the benzyl groups and acidic hydrolysis of the resulting (α-amino-3-piperidinyl)phosphonates (R)-42 and (S)-43 led to enantiopure α-amino-3-piperidinylphosphonic acids (R)-44 and (S)-45 in good yields (Scheme 11).

View Article: PubMed Central - HTML - PubMed

ABSTRACT

Multicomponent reactions (MCRs) are one of the most important processes for the preparation of highly functionalized organic compounds in modern synthetic chemistry. As shown in this review, they play an important role in organophosphorus chemistry where phosphorus reagents are used as substrates for the synthesis of a wide range of phosphorylated heterocycles. In this article, an overview about multicomponent reactions used for the synthesis of heterocyclic compounds bearing a phosphonate group on the ring is given.

No MeSH data available.