Tetrahedron

Regioselective reductive opening of substituted phthalans: synthetic applications

D García, F Foubelo, M Yus

Index: Garcia, Daniel; Foubelo, Francisco; Yus, Miguel Tetrahedron, 2008 , vol. 64, # 19 p. 4275 - 4286

Full Text: HTML

Citation Number: 17

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 ...

Related Articles:

A new synthetic route to 2-hydroxynaphthalene-1-carboxylic acid derivatives. An efficient access to the naphthalene moiety of neocarzinostatin chromophore

[Shishido; Yamashita; Hiroya; Fukumoto; Kametani Tetrahedron, 1989 , vol. 45, # 18 p. 5791 - 5804]

Some evidence in favour of an electron transfer mechanism in the TiO 2 photosensitized oxidation of benzyl derivatives in aqueous media

[Ranchella, Michele; Rol, Cesare; Sebastiani, Giovanni V. Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 2 p. 311 - 315]

A new synthetic route to 2-hydroxynaphthalene-1-carboxylic acid derivatives. An efficient access to the naphthalene moiety of neocarzinostatin chromophore

[Shishido; Yamashita; Hiroya; Fukumoto; Kametani Tetrahedron, 1989 , vol. 45, # 18 p. 5791 - 5804]

Some evidence in favour of an electron transfer mechanism in the TiO 2 photosensitized oxidation of benzyl derivatives in aqueous media

[Ranchella, Michele; Rol, Cesare; Sebastiani, Giovanni V. Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 2 p. 311 - 315]

Some evidence in favour of an electron transfer mechanism in the TiO 2 photosensitized oxidation of benzyl derivatives in aqueous media

[Ranchella, Michele; Rol, Cesare; Sebastiani, Giovanni V. Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 2 p. 311 - 315]

More Articles...