Premium
Synthesis of Fluorine‐Containing Cyclic α‐Amino Acid and α‐Amino Phosphonate Derivatives by Alkene Metathesis
Author(s) -
Osipov Sergey N.,
Artyushin Oleg I.,
Kolomiets Alexey F.,
Bruneau Christian,
Picquet Michel,
Dixneuf Pierre H.
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200110)2001:20<3891::aid-ejoc3891>3.0.co;2-r
Subject(s) - chemistry , phosphonate , alkene , electrophile , metathesis , nucleophile , ring closing metathesis , electrophilic fluorination , amino esters , medicinal chemistry , catalysis , amino acid , stereochemistry , organic chemistry , biochemistry , polymerization , polymer
The electrophilic imino esters XF 2 CC(=NPG)CO 2 Me and imino phosphonates CF 3 CC(=NPG)P(O)(OR) 2 (PG = SO 2 Ph, Cbz, Boc) were transformed by nucleophilic and then electrophilic additions into fluorine‐containing amino esters and amino phosphonates with two pendent alkene chains (XF 2 C)(CH 2 =CH(CH 2 ) n C(NPG)(Z)(CH 2 ) m CH=CH 2 [Z = CO 2 Me, P(O)(OR) 2 ]. The ring‐closing metathesis was performed on the α‐amino ester dienes with Ru=CHPh(Cl) 2 (PCy 3 ) 2 catalyst and afforded five‐, six‐, and seven‐membered cyclic amino esters, whereas the α‐aminophosphonate dienes were transformed with RCM catalyst [Ru=C=C=CPh 2 (Cl)(PCy 3 )( p ‐cymene)]OTf to give six‐ and seven‐membered cyclic α‐amino‐α‐(trifluoromethyl)phosphonates.