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

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Abstract
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)

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