158109-92-3Relevant academic research and scientific papers
The chiral auxiliary N-1-(1′-Naphthyl)ethyl-O-tert- butylhydroxylamine: A chiral weinreb amide equivalent
Chernega, Alexander N.,Davies, Stephen G.,Goodwin, Christopher J.,Hepworth, David,Kurosawa, Wataru,Roberts, Paul M.,Thomson, James E.
supporting information; experimental part, p. 3254 - 3257 (2009/12/05)
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.
