Title: Garner's Aldehyde
CAS Registry Number: 127589-93-9
CAS Name: 4-Formyl-2,2-dimethyl-3-oxazolidinecarboxylic acid 1,1-dimethylethyl ester
Additional Names: 1,1-dimethylethyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate
Molecular Formula: C11H19NO4
Molecular Weight: 229.27
Percent Composition: C 57.63%, H 8.35%, N 6.11%, O 27.91%
Literature References: Both enantiomers are configurationally stable building blocks for use in asymmetric synthesis. Prepn of R-form: P. Garner, Tetrahedron Lett. 25, 5855 (1984); of S-form: P. Garner, J. M. Park, J. Org. Chem. 52, 2361 (1987). Improved prepn of S-form: A. McKillop et al., Synthesis 1994, 31. Review of chemistry: X. Liang et al., J. Chem. Soc. Perkin Trans. 1 2001, 2136-2157.
Derivative Type: R-Form
CAS Registry Number: 95715-87-0
Additional Names: (R)-Garner aldehyde
Properties: [a]D27 +103° (c = 1.0 in CHCl3).
Optical Rotation: [a]D27 +103° (c = 1.0 in CHCl3)
Derivative Type: S-Form
CAS Registry Number: 102308-32-7
Additional Names: (S)-Garner aldehyde
Properties: Colorless liquid, bp1.0-1.4 83-88°; bp0.3 72-75°. [a]D -91.7° (c = 1.34 in CHCl3).
Boiling point: bp1.0-1.4 83-88°; bp0.3 72-75°
Optical Rotation: [a]D -91.7° (c = 1.34 in CHCl3)
Use: Chiral, non-racemic synthon for asymmetric synthesis of amino sugars and other nitrogen-containing targets. |