ROLE OF STERIC, ELECTROSTATIC AND HYDROGEN BONDING EFFECTS AS FACE SELECTIVITY CONTROLLING FACTORS IN NITRONE CYCLOADDITIONS

DOI: 10.1016/S0040-4039(00)95332-2

Source and publish data:

Tetrahedron Letters p. 1225 - 1228 (1987)

Update date:2022-07-30

Topics:

Authors:

Burdisso, Marina

Gandolfi, Remo

Pevarello, Paolo

Rastelli, Augusto

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Article abstract of DOI:10.1016/S0040-4039(00)95332-2

A highly selective syn-attack is promoted by hydrogen bonding effects in the reaction of nitrones with endo-5-hydroxybicyclo<2.2.2>oct-2-enes.By contrast repulsive interactions ( steric and electrostatic) between other kinds of substituents and the attacking nitrone result in an almost exclusive anti selectivity.

Full text of DOI:10.1016/S0040-4039(00)95332-2

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