Addition of N-benzylhydrazine to sugar δ-enlactones

DOI: 10.1016/S0040-4020(01)85245-5

Source and publish data:

Tetrahedron p. 7219 - 7230 (1994)

Update date:2022-08-05

Topics:

Authors:

Panfil Panfil

Krajewski

Gluzinski

Stefaniak

Chmielewski

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Article abstract of DOI:10.1016/S0040-4020(01)85245-5

The conjugate addition - rearrangement of N-benzylhydrazine to sugar δ- enlactone with erythro configuration 1 and 2 affords mixtures of respective ribo and arabino isomers with the former one prevailing. In the case of the threo lactone 3 two regioisomers with xylo configuration are produced, whereas in the case of 4 only one isomer with the erythro configuration is formed. The stereochemical course of these reactions was explained.

Full text of DOI:10.1016/S0040-4020(01)85245-5

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