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

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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 ...