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Long-range substituent effects. The regioselective electrophilic additions of exo-3,6-epoxytetrahydrophthalide and its derivatives.

✍ Scribed by Tarcisio Ferrari; Pierre Vogel

Publisher: Elsevier Science
Year: 1986
Tongue: French
Weight: 141 KB
Volume: 27
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)85251-x

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✦ Synopsis

The regioselectivity of electrophilic additions can be controlled by carboxylate or dialkoxymethyl Under kinetic control, enones 1 add soft electrophiles, EX, to give the corresponding _ adducts 2. --In contrast with 1, their synthetic precursors 3 were found to add EX with the opposite regioselectivity giving the corresponding adducts 4.I** In 1 and 1 the substi-tuents at C(2) are separated by one sp3-hybridized carbon atom. The very high selectivities

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