1177266-16-8

Basic information

• Product Name: 1-acetylnaphthalene-O-tert-butyl oxime
• Synonyms: 1-acetylnaphthalene-O-tert-butyl oxime
• CAS NO: 1177266-16-8
• Molecular Weight: 241.333
• Mol File: 1177266-16-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-acetylnaphthalene-O-tert-butyl oxime(CAS DataBase Reference)
• NIST Chemistry Reference: 1-acetylnaphthalene-O-tert-butyl oxime(1177266-16-8)
• EPA Substance Registry System: 1-acetylnaphthalene-O-tert-butyl oxime(1177266-16-8)

Safety Data

• Hazardous Substances Data: 1177266-16-8(Hazardous Substances Data)

Upstream product

• 1177266-29-3 (2S,1'R)-N-tert-Butoxy-N-1'-(1''-naphthyl)ethyl 2-benzylpent-4-enamide 

Relevant articles and documents

The chiral auxiliary N-1-(1′-Naphthyl)ethyl-O-tert- butylhydroxylamine: A chiral weinreb amide equivalent

The chiral auxiliary N-1-(1′-naphthyl)ethyl-O-terf- 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 (≥94% de) gives the corresponding chiral, 2-substituted derivatives as single diastereoisomers (>98% de) after chromatography. Reductive cleavage with LiAlH4 allows direct access to chiral aldehydes, and treatment with MeLi gives chiral methyl ketones in excellent enantiopurity (≥94% ee). The auxiliary can be recovered in >98% ee and recycled.