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Synlett 1999; 1999(10): 1543-1546
DOI: 10.1055/s-1999-2898
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Lewis Acid Catalyzed Condensation between Glycine Iminoester Enolates and p-Tolylsulfinimines

Alma Viso* , Roberto Fernández de la Pradilla, Ana García, Marta Alonso, Carlos Guerrero-Strachan, Isabel Fonseca
  • *Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense, E-28040 Madrid, Spain; Fax 34-9 15 64 48 53; E-mail: iqofp19@fresno.csic.es
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Publication Date:
31 December 1999 (online)

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In the presence of Lewis acids, p-tolylsulfinimines react with glycine iminoester enolates to produce, after cyclization of open-chain intermediates, enantiopure N-sulfinylimidazolidines with good stereoselectivity. The predominant facial outcome of the process is opposite to most known examples involving enolates and sulfinimines. Two of these adducts have been easily transformed into novel non-symmetrical differentially protected vicinal diamines.

sulfinimines - chiral auxiliaries - asymmetric synthesis - vicinal diamines - amino alcohols