A new route to secondary amines from bis-(alkoxymethyl)-alkylamines - The activation of an aminomethyl group and protection of the product by the same functional group

DOI: 10.1016/S0040-4039(00)97589-0

Source and publish data:

Tetrahedron Letters p. 4229 - 4232 (1990)

Update date:2022-08-04

Topics:

Authors:

Earle, Martyn J.

Fairhurst, Robin A.

Heaney, Harry

Papageorgiou, George

Wilkins, Robert F.

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Article abstract of DOI:10.1016/S0040-4039(00)97589-0

Treatment of N,N-bis(alkoxymethyl)alkylamines with a variety of acidic reagents affords good yields of N-alkoxymethyl-N-alkylmethyleneiminium salts which react with trimethylsilyl enol ethers, and nucleophilic aromatic substrates to form protected secondary amines or tertiary amines by domino reactions; silyl ketene acetals afford tertiary amines only.

Full text of DOI:10.1016/S0040-4039(00)97589-0

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