Enantiomerically pure isoxazolines via addition of nitrile oxides to chiral N-acryloyl toluene-2,α-sultams

DOI: 10.1016/S0040-4039(00)93489-0

Source and publish data:

Tetrahedron Letters p. 4893 - 4896 (1991)

Update date:2022-07-30

Topics: Isolation and Purification Scale-up and optimization

Authors:

Oppolzer

Kingma Kingma

Pillai Pillai

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Article abstract of DOI:10.1016/S0040-4039(00)93489-0

New saccharine-derived, crystalline acryloylsultams 12 undergo efficient 1,3-dipolar cycloadditions of nitrile oxides with ≥ 95:5 stereoface discrimination. Products 13 or 14 are purified by simple crystallization and cleaved with recovery of the chirophore to provide optically pure Δ²-isoxazolines 15.

Full text of DOI:10.1016/S0040-4039(00)93489-0

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