Highly Diastereoselective Addition of Ketone Enolates to N-Sulfinyl Imines: Asymmetric Synthesis of syn- and anti-1,3-Amino Alcohol Derivatives

Andrew Kennedy; Adam Nelson; Alexis Perry

doi:10.1055/s-2004-820050

LETTER

Highly Diastereoselective Addition of Ketone Enolates to N-Sulfinyl Imines: Asymmetric Synthesis of syn- and anti-1,3-Amino Alcohol Derivatives

Andrew Kennedy^a, Adam Nelson*^b, Alexis Perry^b
^a GlaxoSmithKline, Old Powder Mills, Nr Leigh, Tonbridge, Kent, TN11 9AN, UK
^b School of Chemistry, University of Leeds, Leeds, LS2 9JT, UK
Fax: +44(113)3436565; e-Mail: adamn@chem.leeds.ac.uk;

Abstract

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Abstract

Lithium enolates derived from ketones may be added to N-sulfinyl imines with high diastereoselectivity. Diastereoselective reduction gave either the syn- or anti-1,3-amino alcohol derivative.

Key words

asymmetric synthesis - chiral auxiliaries - amino alcohols - stereoselective synthesis

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References

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