Simple Aziridino Alcohols as Chiral Ligands. Enantioselective Additions of Diethylzinc to N-Diphenylphosphinoylimines

Pher G. Andersson; David Guijarro; David Tanner

doi:10.1055/s-1996-5529

Synlett 1996; 1996(8): 727-728
DOI: 10.1055/s-1996-5529

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Simple Aziridino Alcohols as Chiral Ligands. Enantioselective Additions of Diethylzinc to N-Diphenylphosphinoylimines

Pher G. Andersson¹ , David Guijarro, David Tanner²

¹Department of Organic Chemistry, Uppsala University, Box 531, S-751 21 Uppsala, Sweden
²Department of Organic Chemistry, The Technical University of Denmark, Building 201, DK-2800, Lyngby, Denmark

Abstract

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Simple chiral aziridino alcohols 2-5, easily available from L-serine, L-threonine or L-allo-threonine, have been used as ligands to promote the addition of Et₂Zn to the diphenylphosphinoylimine 1 (Ar=Ph). Enantioselectivities of up to 94% could be obtained by proper choice of the substituents on the ligand. Up to 90% of the ligand could be recovered during the work-up. The use of ligand 3a as catalyst for the same reaction has also been studied.

Diethylzinc - N-diphenylphosphinoylimines - aziridino alcohols - chiral amine - enantioselective addition

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