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Self‐Assembly of Chiral 1,8‐Diaza‐3,6,10,13‐tetraphosphacyclotetradecanes via Dynamic Transformation of 7‐ and 14‐Membered Aminomethylphosphines
Author(s) -
Musina Elvira,
Wittmann Tatiana,
Latypov Shamil,
Kondrashova Svetlana,
Lönnecke Peter,
Litvinov Igor,
HeyHawkins Evamarie,
Karasik Andrey
Publication year - 2019
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201900386
Subject(s) - chemistry , diastereomer , enantiomer , stereochemistry , butylamine , chirality (physics) , enantioselective synthesis , amine gas treating , organic chemistry , chiral symmetry , catalysis , physics , quantum mechanics , nambu–jona lasinio model , quark
Chiral 1,8‐diaza‐3,6,10,13‐tetraphosphacyclotetradecanes were obtained by condensation of 1,2‐bis(phenylphosphanyl)ethane, paraformaldehyde and optically pure ( S )‐(+)‐ sec ‐butylamine or racemic sec ‐butylamine. The covalent self‐assembly stereoselectively led to only one enantiomer, 14‐P 4 SSSS C 2 SS , starting with the optically pure sec ‐butylamine, and to two enantiomeric pairs, 14‐P 4 SSSS C 2 SS /14‐P 4 RRRR C 2 RR and 14‐P 4 SSSS C 2 RS /14‐P 4 RRRR C 2 RS , when employing the racemic sec ‐butylamine. It was demonstrated that all stereoisomers undergo dynamic transformation into three diastereomers of 7‐membered cycles: two stereoisomers with the same configuration ( rac ) and one isomer with different configuration of the phosphorus atoms ( meso form) of both phosphorus atoms.