α-CF3-Substituted Phosphorus Containing Analogs of α-Amino Acids. Novel Six- and Seven-Membered α-Amino Phosphonates via Ring Closing Metathesis with LnRu=C=C=CR2 Precatalyst

Sergey N. Osipov; Oleg I. Artyushin; Alexey F. Kolomiets; Christian Bruneau; Pierre H. Dixneuf

doi:10.1055/s-2000-6650

Synlett 2000; 2000(7): 1031-1033
DOI: 10.1055/s-2000-6650

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α-CF₃-Substituted Phosphorus Containing Analogs of α-Amino Acids. Novel Six- and Seven-Membered α-Amino Phosphonates via Ring Closing Metathesis with LnRu=C=C=CR₂ Precatalyst

Sergey N. Osipov^* , Oleg I. Artyushin, Alexey F. Kolomiets, Christian Bruneau, Pierre H. Dixneuf

^*A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, 117813 Moscow, V-334, GSP-1, Russia; E-mail: osipov@ineos.ac.ru

Abstract

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α-CF₃-substituted α-amino phosphonates with two alkene chains, 1,7-dienes and 1,8-dienes, were obtained by nucleophilic addition to highly electrophilic imines PG-N=C(CF₃)P(O)(OR)₂. They were treated with the ring closing metathesis catalyst [Ru=C=C=CPh₂(Cl)(PCy₃)₂ (p-cymene)]OTf to give the α-CF₃-substituted phosphorus-containing analogs of dehydropipecolinic and tetrahydroazepin-2-carboxylic acids.

phosphonates - imines - ring closing metathesis

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