Cobalt-mediated alkylation of (4R) and (4S)-3-acetoacetyl-4-benzyloxazolidin-2-ones. Preparation of enantiopure diphenylmethyl-, 9-fluorenyl-, and (1-adamantyl)glycines

DOI: 10.1016/0040-4039(96)01322-6

Source and publish data:

Tetrahedron Letters p. 6197 - 6200 (1996)

Update date:2022-09-26

Topics:

Authors:

Galvez, Nicanor

Moreno-Manas, Marcial

Vallribera, Adelina

Molins, Elies

Cabrero, Araceli

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Article abstract of DOI:10.1016/0040-4039(96)01322-6

The Co(II) complexes of (4R) and (4S)-3-acetoacetyl-4-benzyloxazolidin-2-ones are alkylated diastereoselectively with diphenylmethyl, 9-fluorenyl, and 1-adamantyl bromide. The resulting products are converted into enantiopure α-substituted glycines. Similar results are obtained by alkylation of the free acetoacetyloxazolidinones under Co(II)-catalysis.

Full text of DOI:10.1016/0040-4039(96)01322-6

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