LiClO4-Induced Mannich Reaction − Diastereo- and Enantioselective Synthesis of β-Amino Ketones by Addition of Enamines, Imines or Silylenolethers to Aldehydes and Dialkyltrimethylsilylamines

✍ Scribed by Afshin Zarghi; M. Reza Naimi-Jamal; Sarah A. Webb; Said Balalaie; M. Reza Saidi; Junes Ipaktschi

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 389 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199801)1998:1<197::aid-ejoc197>3.0.co;2-r

✦ Synopsis

LiClO 4 -mediated one-pot reactions of aldehydes with (tri-thiophene-2-carbaldehyde, high diasteroselectivity was achieved, the aminoalkylation of aliphatic aldehydes such as methylsilyl)dialkylamines 2, 5 or 19 and C nucleophiles such as enamines 3, 10 and 12, imines 7 and 11 or (trimethylsilyl)-isobutyraldehyde and pivalaldehyde lacked diastereoselectivity. Enantioselective Mannich reactions using chiral en-enol ethers 8 and 9 afforded the corresponding aminoalkylation products in high yields. Whereas by using aromatic al-amines 22 and 23 are reported. dehydes, such as benzaldehyde, pyridine-3-carbaldehyde or