GARNER ALDEHYDE SPECTRAL DATA
1H (CDCl3, 300 MHz)
9.62 and 9.55 (1H, br s, CHO),
4.36 and 4.20 (1H, m), 4.09 (2H, m),
1.63 and 1.60 (3H, s),
1.57 and 1.51 (3H, s),
1.52 and 1.45 (9H, s).
Most peaks are doubled due to restricted rotation of NBOC group.
IR (thin film, cm-1) 1740 (CHO), 1710 (BOC).
Reference
P. Garner and J. M. Park, Org Synth. 1991, 70, 18.
Other References
P. Garner and J. M. Park, J. Org. Chem. 1987, 52, 2361 doi:10.1021/jo00388a004
A. McKillop, R. J. K. Taylor, R. J. Watson and N. Lewis, Synthesis, 1994, 31 doi:10.1055/s-1994-25398
A. Dondoni and D. Perrone, Synthesis 1997, 527 doi:10.1055/s-1997-1229
A. McKillop, R. J. K. Taylor, R. J. Watson and N. Lewis, Synthesis, 1994, 31 doi:10.1055/s-1994-25398
A. Dondoni and D. Perrone, Synthesis 1997, 527 doi:10.1055/s-1997-1229
J.O.C. 1997, 62, 4293.
J.O.C. 1988, 53, 4395.
J.O.C. 1986, 51, 2609.
J.O.C. 1988, 53, 4395.
J.O.C. 1986, 51, 2609.
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 ofR-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.
