C-silylation of secondary amides: GlcNAc peracetate derivatives

DOI: 10.1016/0040-4039(95)01559-0

Source and publish data:

Tetrahedron Letters p. 7395 - 7398 (1995)

Update date:2022-08-03

Topics:

Authors:

Werner, R. Marshall

Barwick, Michael

Davis, Jeffery T.

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Article abstract of DOI:10.1016/0040-4039(95)01559-0

The Me₃SiOTf-promoted formation of GlcNAc 1,2-cis oxazoline from GlcNAc peracetates can give significant amounts of nonpolar by-products. We identified these by-products to be C-silylated esters and amides. Secondary amides are readily C-silylated by treatment with a mixture of Me₃SIOTf and NEt₃. These C-silylated secondary amides are useful, as they undergo fluoride ion promoted aldol condensation.

Full text of DOI:10.1016/0040-4039(95)01559-0

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