Photo: Public Domain
Ref:
"TMS-Cyclopentene Annulation: A Regiocontrolled Approach to the Synthesis of Five-Membered Rings", R. L. Danheiser, D. J. Carini, and A. Basak, J. Am. Chem. Soc. 1981, 103, 1604.
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Sunday, November 13, 2011
11/13/11 - Danheiser Annulation
A reaction of ring making significance; this reaction is used to create a cyclopentane from a silylallene and a conjugated ketone system (α,β-unsaturated ketone). The mechanism must be in the presence of a lewis acid in order to proceed, and in most cases TiCl2 is used along with a dichloromethane solvent. In this particular mechanism below the α,β-unsaturated ketone is introduced to the trialkylsilylallene to produce the trialkylsilylcyclopentene molecule.
Ref:
"TMS-Cyclopentene Annulation: A Regiocontrolled Approach to the Synthesis of Five-Membered Rings", R. L. Danheiser, D. J. Carini, and A. Basak, J. Am. Chem. Soc. 1981, 103, 1604.
Ref:
"TMS-Cyclopentene Annulation: A Regiocontrolled Approach to the Synthesis of Five-Membered Rings", R. L. Danheiser, D. J. Carini, and A. Basak, J. Am. Chem. Soc. 1981, 103, 1604.
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