Diastereoselective intramolecular additions of allyl- and propargylsilanes to iminium ions: synthesis of cyclic and bicyclic quaternary amino acids.
Chiral imino lactones derived from (R)-phenylglycinol containing an allyl- or propargyltrimethylsilyl group in the side chain readily cyclized in the presence of acidic reagents to afford spirocyclic compounds with high diastereoselectivity. Removal of the chiral auxiliary produced 2-substituted 1-aminocycloalkanecarboxylic acids, whereas further cyclizations by means of metathesis or hydroamination reactions led to bicyclic derivatives of pipecolic acid and proline.
Fustero
Santos
S
Departamento de Química Orgánica, Universidad de Valencia, E-46100 Burjassot, Spain. santos.fustero@uv.es
Mateu
Natalia
N
Simón-Fuentes
Antonio
A
Aceña
José Luis
JL
D000480:Alkynes / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007097:Imines / Q000737:chemistry*; D007477:Ions / Q000737:chemistry; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D000498:Allyl Compounds; D000596:Amino Acids; D007097:Imines; D007477:Ions; D012821:Silanes