Diastereodivergent Synthesis of Fluorinated Cyclic β(3)-Amino Acid Derivatives.
The ability of 2-p-tolylbenzyl carbanions to behave as a source of chiral benzylic nucleophiles has been shown in its reaction with fluorinated imines. The process takes place with high levels of stereocontrol, rendering the corresponding amines as single diastereoisomers. Subsequent cross-metathesis followed by intramolecular aza-Michael reaction makes the synthesis of fluorinated homoproline derivatives bearing three stereogenic centers possible. Furthermore, the selectivity of the cyclization process can easily be tuned up in a diastereodivergent manner simply by changing the reaction conditions.
Departamento de Química Orgánica Universidad de Valencia , 46100 Burjassot, Spain.
Isabel
I
Aparici
Departamento de Química Orgánica Universidad de Valencia , 46100 Burjassot, Spain.
Marta
M
Guerola
Departamento de Química Orgánica Universidad de Valencia , 46100 Burjassot, Spain.
Clemens
C
Dialer
Departamento de Química Orgánica Universidad de Valencia , 46100 Burjassot, Spain.
Antonio
A
Simón-Fuentes
Departamento de Química Orgánica Universidad de Valencia , 46100 Burjassot, Spain.|Centro de Investigación Príncipe Felipe, Laboratorio de Moléculas Orgánicas , 46012 Valencia, Spain.
María
M
Sánchez-Roselló
Departamento de Química Orgánica Universidad de Valencia , 46100 Burjassot, Spain.
Carlos
C
del Pozo
Departamento de Química Orgánica Universidad de Valencia , 46100 Burjassot, Spain.|Centro de Investigación Príncipe Felipe, Laboratorio de Moléculas Orgánicas , 46012 Valencia, Spain.
Santos
S
Fustero
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011392:Proline / Q000031:analogs & derivatives / Q000737:chemistry
D000596:Amino Acids; D006845:Hydrocarbons, Fluorinated; D011392:Proline; C010983:homoproline