title: Stereoselective organocatalytic one-pot α,α-bifunctionalization of acetaldehyde by a tandem Mannich reaction/electrophilic amination.
abstract: The first asymmetric organocatalyzed one-pot α,α-bifunctionalization of acetaldehyde with two different electrophiles is described. A diarylprolinol silyl ether-catalyzed reaction of acetaldehyde with an imine and di-tert-butyl azodicarboxylate affords syn-2,3-diaminoalcohols with excellent ee values of up to 98%. This methodology was successfully applied to the synthesis of a chiral α,β-diaminocarboxylic acid.
authors: Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles-St-Quentin-en-Yvelines, 45 Avenue des États-Unis, 78035 Versailles cedex, France.
authors: Vincent
authors: V
authors: Coeffard
authors: Alaric
authors: A
authors: Desmarchelier
authors: Bénédicte
authors: B
authors: Morel
authors: Xavier
authors: X
authors: Moreau
authors: Christine
authors: C
authors: Greck