Asymmetric Mannich‐Type Reaction of a Chiral N‐(tert‐Butylsulfinyl) Ketimine with Imines: Application to the Synthesis of Chiral 1,3‐Diamines

Deprotonation of the chiral N ‐( tert ‐butylsulfinyl) ketimine 1 followed by trapping with imines 2 afforded the β‐aminoimines 3 as the Mannich‐type products in high diastereoselectivities (99:1 dr ). As versatile synthons chiral β‐amino imines 3 could be transformed into enantiomeric β‐amino ketone and chiral syn ‐ or anti ‐1,3‐diamines with high diastereomeric excess by hydrolysis or reduction, respectively. Moreover, the nucleophilic addition of organometallicreagents to chiral β‐amino imines 3 could provide 1,1,3‐trisubstituted 1,3‐diamines with high diastereoselectivities. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)