Tetrahedron

Bi (III) halides as efficient catalysts for the O-acylative cleavage of tetrahydrofurans: an expeditious entry to tetralins

SJ Coles, JF Costello, WN Draffin, MB Hursthouse…

文献索引：Coles, Simon J.; Costello, James F.; Draffin, William N.; Hursthouse, Michael B.; Paver, Simon P. Tetrahedron, 2005 , vol. 61, # 18 p. 4447 - 4452

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被引用次数: 18

摘要

The mild (DCM/20° C), quantitative, regioselective, O-acylative cleavage of tetrahydrofurans using organic acid halides with catalytic Bi (III) halides is reported. X-ray crystallography is used to rationalise the failure of the reaction in the case of certain crowded acid chlorides, and a useful aspect of chemoselectivity is revealed. The synthetic potential of this reaction is illustrated with a highly efficient O-acylative cleavage/intramolecular alkylation approach ...