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LiClO 4 ‐Induced Mannich Reaction − Diastereo‐ and Enantioselective Synthesis of β‐Amino Ketones by Addition of Enamines, Imines or Silylenolethers to Aldehydes and Dialkyltrimethylsilylamines
Author(s) -
Zarghi Afshin,
NaimiJamal M. Reza,
Webb Sarah A.,
Balalaie Said,
Saidi M. Reza,
Ipaktschi Junes
Publication year - 1998
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/(sici)1099-0690(199801)1998:1<197::aid-ejoc197>3.0.co;2-r
Subject(s) - chemistry , enantioselective synthesis , benzaldehyde , isobutyraldehyde , organic chemistry , mannich reaction , enol , trimethylsilyl , nucleophile , trimethylsilyl cyanide , aldehyde , pyridine , aldimine , medicinal chemistry , catalysis
LiClO 4 ‐mediated one‐pot reactions of aldehydes with (trimethylsilyl)dialkylamines 2 , 5 or 19 and C nucleophiles such as enamines 3 , 10 and 12 , imines 7 and 11 or (trimethylsilyl)enol ethers 8 and 9 afforded the corresponding aminoalkylation products in high yields. Whereas by using aromatic aldehydes, such as benzaldehyde, pyridine‐3‐carbaldehyde or thiophene‐2‐carbaldehyde, high diasteroselectivity was achieved, the aminoalkylation of aliphatic aldehydes such as isobutyraldehyde and pivalaldehyde lacked diastereoselectivity. Enantioselective Mannich reactions using chiral enamines 22 and 23 are reported.