Reductive alkylation of aromatic amines with enol ethers

Reductive alkylation of aromatic amines with 2-methoxypropene using 1.0 equivalent of HOAc and NaBH(OAc)(3) in 1,2-dichloroethane (DCE) at room temperature furnished N-isopropyl amines in 50-98% yields. This method was successfully extended to trimethylsilyl enol ethers. The mild reaction conditions...

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Bibliographic Details
Published inSynlett no. 4; pp. 583 - 586
Main Authors Reddy, TJ, Leclair, M, Proulx, M
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 04.03.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CATALYSIS
sodium triacetoxyborohydride
ACIDS
ALDEHYDES
aromatic amines
5-HT4 RECEPTOR
KETONES
AMINATION
POTENT
2-methoxypropene
trimethylsilylenol ethers
MONOALKYLATION
reductive alkylation
DERIVATIVES
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Summary:Reductive alkylation of aromatic amines with 2-methoxypropene using 1.0 equivalent of HOAc and NaBH(OAc)(3) in 1,2-dichloroethane (DCE) at room temperature furnished N-isopropyl amines in 50-98% yields. This method was successfully extended to trimethylsilyl enol ethers. The mild reaction conditions provide a new alternative procedure for the reductive amination of electron deficient aromatic amines.
ISSN:0936-5214
DOI:10.1055/s-2005-863704