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2005
Amines
Q 0120
32- 087
Reductive Alkylation of Aromatic Amines with Enol Ethers. — A simple,
high-yielding modification to the standard reductive amination protocol is developed
working particularly well for the preparation of N-alkylated aromatic amines. Reductive alkylation with 2-methoxypropene (IIa) is much faster than with acetone and
2,2-dimethoxypropane. Utilizing (IIa) under reductive amination conditions provides
the N-isopropyl aromatic amines (V). This method is extended to trimethylsilyl enol
ethers (IIb)—(IId). It is the method of choice for reductive amination of weakly nucleophilic aromatic amines and sterically hindered unreactive carbonyl compounds. —
(REDDY*, T. J.; LECLAIR, M.; PROULX, M.; Synlett 2005, 4, 583-586; ViroChem
Pharma Inc., Laval, Que. H7V 4A7, Can.; Eng.) — H. Hoennerscheid
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