Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
LiClO4-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.
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