Epoxidation of 5-(Tosylamido)-3-hexen-2-ol Derivatives. Stereochemical Assignment of Product Configuration by NMR and Molecular Mechanics Studies

DOI: 10.1021/jo00048a044

Source and publish data:

Journal of Organic Chemistry p. 6025 - 6031 (1992)

Update date:2022-08-04

Topics:

Authors:

Pettersson, Helena

Gogoll, Adolf

Baeckvall, Jan-E.

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Article abstract of DOI:10.1021/jo00048a044

Epoxidation of syn- and anti-5-(tosylamido)-3-hexen-2-ol derivatives was studied using three different epoxidation reagents: (i) m-CPBA, (ii) t-BuOOH/VO(acac)2, and (iii) t-BuOOH/Ti(O-i-Pr)4.A method for the stereochemical assignment of the 3,4-epoxy-5-(tosylamido)-3-hexen-2-ol derivatives obtained was developed by the use of NMR spectroscopy.

Full text of DOI:10.1021/jo00048a044

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Product name:(2S*,3R*,4S*,5S*)-2-acetoxy-3,4-epoxy-5-(tosylamido)hexane

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