Synthesis of cyclic and acyclic beta-amino acids via chelation-controlled 1,3-dipolar cycloaddition.
Isoxazolidines have been synthesized in diastereomeric excess up to 94% via a MgBr2-induced chelation-controlled 1,3-dipolar cycloaddition reaction with N-hydroxyphenylglycinol as a chiral auxiliary. The diastereomerically pure isoxazolidines were further transformed into cyclic and acyclic beta-amino acid derivatives.
Hanselmann
Roger
R
Bristol-Myers Squibb Pharma Company, Experimental Station, E 336/36, P.O. Box 80336, Wilmington, Delaware 19880-0336, USA. Hanselmann@Rib-X.com
Zhou
Jiacheng
J
Ma
Philip
P
Confalone
Pat N
PN
D000144:Acids, Acyclic / Q000138:chemical synthesis*; D000588:Amines / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D002614:Chelating Agents / Q000737:chemistry; D003500:Cyclization; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D007555:Isoxazoles / Q000737:chemistry; D009589:Nitrogen Oxides / Q000737:chemistry; D013237:Stereoisomerism
D000144:Acids, Acyclic; D000588:Amines; D000596:Amino Acids; D002614:Chelating Agents; D007555:Isoxazoles; D009589:Nitrogen Oxides; C015388:nitrones; C021316:N-phenylglycine; D005998:Glycine