Alternating stereoselective self-assembly of SSSS/RRRR or RSSR isomers of tetrakisphosphines in the row of 14-, 16-, 18- and 20-membered macrocycles

Novel 18- and 20-membered P,N-macrocycles have been obtained stereoselectively by covalent self-assembly of α,ω-bisphosphines, formaldehyde and benzylamine. Alternating SSSS/RRRR or RSSR diastereomers were formed in the row of the 14-, 16-, 18- and 20-membered macrocyclic aminomethylphosphines. For...

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Bibliographic Details
Published in:Dalton transactions : an international journal of inorganic chemistry 2014-09, Vol.43 (33), p.12784-12789
Main Authors: Naumov, Roman N, Musina, Elvira I, Kanunnikov, Kirill B, Fesenko, Tatiana I, Krivolapov, Dmitry B, Litvinov, Igor A, Lönnecke, Peter, Hey-Hawkins, Evamarie, Karasik, Andrey A, Sinyashin, Oleg G
Format: Article
Language:English
Subjects:
Atomic properties
Covalence
Formaldehyde
Macrocyclic compounds
Methylene
Phosphorus
Self assembly
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Summary:Novel 18- and 20-membered P,N-macrocycles have been obtained stereoselectively by covalent self-assembly of α,ω-bisphosphines, formaldehyde and benzylamine. Alternating SSSS/RRRR or RSSR diastereomers were formed in the row of the 14-, 16-, 18- and 20-membered macrocyclic aminomethylphosphines. For the first time it was demonstrated that the stereochemical result of the reaction depends on the even or odd number of the methylene groups between the two chiral phosphorus atoms in the initial α,ω-bisphosphines.
ISSN:1477-9226
1477-9234
DOI:10.1039/c4dt01619j