American Chemical Society
ol202340p_si_001.pdf (2.25 MB)

Stereoselective Organocatalytic One-Pot α,α-Bifunctionalization of Acetaldehyde by a Tandem Mannich Reaction/Electrophilic Amination

Download (2.25 MB)
journal contribution
posted on 2011-11-04, 00:00 authored by Vincent Coeffard, Alaric Desmarchelier, Bénédicte Morel, Xavier Moreau, Christine Greck
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.