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The chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine is readily prepared from N-hydroxyphthalimide in four steps, with resolution giving access to both enantiomers in > 98% ee, on a multigram (> 25 g) scale. Conversion to a range of N-acyl derivatives, followed by highly diastereoselective alkylation (> or = 94% de) gives the corresponding chiral, 2-substituted derivatives as single diastereoisomers (> 98% de) after chromatography. Reductive cleavage with LiAlH(4) allows direct access to chiral aldehydes, and treatment with MeLi gives chiral methyl ketones in excellent enantiopurity (> or = 94% ee). The auxiliary can be recovered in > 98% ee and recycled.

Original publication

DOI

10.1021/ol901174t

Type

Journal article

Journal

Org Lett

Publication Date

06/08/2009

Volume

11

Pages

3254 - 3257

Keywords

Acylation, Amides, Crystallography, X-Ray, Hydroxylamine, Molecular Structure, Naphthalenes, Stereoisomerism