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Asymmetric Mannich‐Type Reaction of a Chiral N ‐( tert ‐Butylsulfinyl) Ketimine with Imines: Application to the Synthesis of Chiral 1,3‐Diamines
Author(s) -
Zhao CuiHua,
Liu Li,
Wang Dong,
Chen YongJun
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600147
Subject(s) - chemistry , diastereomer , synthon , enantioselective synthesis , chiral auxiliary , enantiomer , deprotonation , mannich reaction , ketone , imine , nucleophile , enantiomeric excess , nucleophilic addition , hydrolysis , medicinal chemistry , chiral derivatizing agent , organic chemistry , combinatorial chemistry , stereochemistry , catalysis , chiral column chromatography , ion
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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