Tetrahedron p. 3365 - 3374 (1995)
Update date:2022-07-30
Topics:
Almena, Juan
Foubelo, Francisco
Yus, Miguel
The reaction of isochroman (1) with an excess of lithium powder and a catalytic amount of DTBB (2.5 mol %) in THF at 20°C yields the title intermediate, which by reaction with different electrophiles (H2O, D2O, CO2 and carbonyl compounds) at temperatures ranging between -78 and 20°C yields, after hydrolysis, the corresponding products 3. Diols 3h-m, derived from benzaldehyde or ketones, give upon treatment with 85% phosphoric acid the corresponding benzoxepines 5h-m. In the other cases, Friedel-Crafts products resulting from a rearrangement of the first carbenium ion formed, are obtained.
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(1998)Doi:10.1248/cpb.43.901
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(1995)Doi:10.1002/anie.201408910
(2015)Doi:10.1021/jm00018a015
(1995)