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Electron deficient dienes I. Normal and inverse electron demand Diels-Alder reaction of the same carbon skeleton

✍ Scribed by Graham J. Bodwell; Zulan Pi

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 287 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(96)02340-4

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✦ Synopsis

The synthesis of compound 11, which features a diene moiety bearing electron withdrawing groups at the l and 3 positions, and its completely regiosdective inverse electron demand Diels-Alder reactions with 1,1-diethoxyethylene, ethyl vinyl ether and styrene are described. Endo addition is preferred. The direct synthetic precursor of 11, in which one of the electron withdrawing groups (a ketone) is protected, participates in normal electron demand Diels-Alder reactions with 1,4naphthoquinone aml N-phenylmaleimide, but is anreactive towards 1,1Miethoxyethylene.

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