A beta-lactone route to chiral gamma-substituted alpha-amino acids: application to the concise synthesis of (S)-alpha-azidobutyro lactone and a natural amino acid.
[reaction: see text] Beta-lactones are useful synthetic intermediates allowing access to a number of functional arrays. In this report, enantiomerically pure 4-trichloromethyl-2-oxetanone is shown to be a versatile amino acid synthon leading to a variety of gamma-substituted alpha-amino acid precursors. The utility of this methodology was demonstrated by the concise synthesis of a protected homoserine equivalent, alpha-azidobutyro lactone, and a naturally occurring alpha-amino acid from the seeds of Blighia unijugata.
Tennyson
Reginald L
RL
Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, Texas 77842-3012, USA.
Cortez
Guillermo S
GS
Galicia
Héctor J
HJ
Kreiman
Charles R
CR
Thompson
Christina M
CM
Romo
Daniel
D
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D000447:Aldehydes; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001386:Azides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D010944:Plants / Q000737:chemistry; D012639:Seeds / Q000737:chemistry
D000447:Aldehydes; D000596:Amino Acids; D001386:Azides; D007202:Indicators and Reagents; D007783:Lactones; C451483:alpha-azidobutyrolactone; D015107:4-Butyrolactone