Role of the countercation in diastereoselective alkylations of pyramidalized bicyclic serine enolates. An easy approach to alpha-benzylserine.
The use of a chiral serine equivalent as an excellent chiral building block has been demonstrated in the synthesis of alpha-benzylserine through a diastereoselective lithium enolate alkylation reaction and subsequent acid hydrolysis. The role of a coordinating countercation (lithium) in the alkylation reaction has been investigated. Theoretical studies have been performed in order to elucidate the stereochemical outcome of the alkylation process, which occurs with total retention of configuration.
Jiménez-Osés
Gonzalo
G
Departamento de Química, Universidad de La Rioja, Grupo de Síntesis Química de La Rioja, UA-CSIC, 26006 Logroño, Spain.
Aydillo
Carlos
C
Busto
Jesús H
JH
Zurbano
María M
MM
Peregrina
Jesús M
JM
Avenoza
Alberto
A
D000478:Alkylation; D001593:Benzyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001593:Benzyl Compounds; C521837:alpha-benzylserine; D012694:Serine