4371. Garner's Aldehyde

Nomenclature

CAS number: 127589-93-9
4-Formyl-2,2-dimethyl-3-oxazolidinecarboxylic acid 1,1-dimethylethyl ester; 1,1-dimethylethyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate.
C11H19NO4; mol wt 229.27.
C 57.63%, H 8.35%, N 6.11%, O 27.91%.

Description and 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.

Chemical structure

Derivative

R-Form.

Nomenclature

CAS number: 95715-87-0
(R)-Garner aldehyde.

Properties

[α]D27 +103° (c = 1.0 in CHCl3).

Derivative

S-Form.

Nomenclature

CAS number: 102308-32-7
(S)-Garner aldehyde.

Properties

Colorless liquid, bp1.0-1.4 83-88°; bp0.3 72-75°. [α]D 91.7° (c = 1.34 in CHCl3).

Use

Chiral, non-racemic synthon for asymmetric synthesis of amino sugars and other nitrogen-containing targets.