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Updated: Feb 2, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Chiral [16]-ane P4N2 macrocycles: stereoselective synthesis and unexpected intermolecular exchange of endocyclic
E I Musina1, R N Naumov, K B Kanunnikov
1A.E. Arbuzov Institute of Organic and Physical Chemistry - Subdivision of FIC KazanSC of RAS, Arbuzov str., 8, Kazan, Russia. elli@iopc.ru.
Abstract:
Chiral 1,9-diaza-3,7,11,15-tetraphosphacyclohexadecanes were stereoselectively synthesized as pure RPSPSPRP isomers via a one-pot Mannich-type condensation reaction of 1,3-bis(arylphosphino)propane, formaldehyde and optically active, as well as racemic, primary amines. An unprecedented intermolecular exchange of endocyclic amino fragments of 1,9-diaza-3,7,11,15-tetraphosphacyclohexadecanes was observed. The lability of the P-CH2-N fragment in macrocyclic aminomethylphosphines is the reason of the stereoisomerization, formation of products with medium-sized cycles as well as the exchange of endocyclic amino fragments. The mechanism of these transformations involving the formation of a methylenephosphonium intermediate and further intra- and intermolecular nucleophilic substitution is discussed.
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