Tetrahedron p. 4167 - 4194 (2010)
Update date:2022-08-04
Topics:
Chernega, Alexander N.
Davies, Stephen G.
Fletcher, Ai M.
Goodwin, Christopher J.
Hepworth, David
Prasad, R. Shyam
Roberts, Paul M.
Savory, Edward D.
Smith, Andrew D.
Thomson, James E.
Treatment of a range of O-protected glycolate derivatives of the chiral auxiliary N-1-(1′-naphthyl)ethyl-O-tert-butylhydroxylamine with KHMDS in the presence of 18-crown-6 followed by addition of an alkyl halide generates α-substituted derivatives with very high levels of diastereoselectivity. Alternatively, reaction of the potassium enolate of a propanoate or O-protected glycolate derivative of N-1-(1′-naphthyl)ethyl-O-tert-butylhydroxylamine with a range of aldehydes gives syn-aldol products with high levels of diastereoselectivity. These adducts may be reductively cleaved with LiAlH4 to give enantiopure α-alkoxy-, α-substituted-β-alkoxy- and α,β-dialkoxyaldehydes in good yield.
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