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

Nicanor Gálvez; Marcial Moreno-Mañas; Adelina Vallribera; Elies Molins; Araceli Cabrero

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

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

Nicanor Gálvez, Marcial Moreno-Mañas, Adelina Vallribera, Elies Molins, Araceli Cabrero

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

16 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	6197-6200
Journal	Tetrahedron Letters
Volume	37
Issue number	34
DOIs	https://doi.org/10.1016/0040-4039(96)01322-6
Publication status	Published - 19 Aug 1996

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@article{71a30280d23846f58ec01c435f835013,

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

abstract = "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.",

author = "Nicanor G{\'a}lvez and Marcial Moreno-Ma{\~n}as and Adelina Vallribera and Elies Molins and Araceli Cabrero",

year = "1996",

month = aug,

day = "19",

doi = "10.1016/0040-4039(96)01322-6",

language = "English",

volume = "37",

pages = "6197--6200",

number = "34",

}

Cobalt-mediated alkylation of (4R) and (4S)-3-acetoacetyl-4-benzyloxazolidin-2-ones. Preparation of enantiopure diphenylmethyl-, 9-fluorenyl-, and (1-adamantyl)glycines. / Gálvez, Nicanor; Moreno-Mañas, Marcial; Vallribera, Adelina; Molins, Elies; Cabrero, Araceli.

In: Tetrahedron Letters, Vol. 37, No. 34, 19.08.1996, p. 6197-6200.

Research output: Contribution to journal › Article › Research › peer-review

TY - JOUR

T1 - Cobalt-mediated alkylation of (4R) and (4S)-3-acetoacetyl-4-benzyloxazolidin-2-ones. Preparation of enantiopure diphenylmethyl-, 9-fluorenyl-, and (1-adamantyl)glycines

AU - Gálvez, Nicanor

AU - Moreno-Mañas, Marcial

AU - Vallribera, Adelina

AU - Molins, Elies

AU - Cabrero, Araceli

PY - 1996/8/19

Y1 - 1996/8/19

N2 - 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.

AB - 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.

U2 - 10.1016/0040-4039(96)01322-6

DO - 10.1016/0040-4039(96)01322-6

M3 - Article

VL - 37

SP - 6197

EP - 6200

IS - 34

ER -