| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5228705 | Tetrahedron | 2008 | 12 Pages |
Abstract
The reductive opening of substituted phthalans 6, 11, 12, 20, 21 and 28 with lithium and a catalytic amount of DTBB leads to the formation of corresponding functionalised organolithium intermediates 8, 15, 16, 23, 25 and 29+30 in a regioselective manner. The further reaction of these dianions with different electrophiles, mainly carbonyl compounds, gives the expected functionalised benzylic alcohols 9, 17, 18, 24, 26 and 31+32. The observed stereochemistry can be easily explained taking into account the values of the electron densities deduced by semiempirical PM3 calculations.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Daniel GarcÃa, Francisco Foubelo, Miguel Yus,