F. Huerta, Cecilia Gómez, A. Guijarro
Mar 13, 1995
Citations
0
Influential Citations
25
Citations
Journal
Tetrahedron
Abstract
Abstract The reaction of 2,3-dichloropropene ( 1 ) and different carbonyl compounds ( 2 ) with an excess of lithium powder (1:7 molar ratio) in the presence of a catalytic amount of DTBB (5 mol %) in THF at 0°C leads, after hydrolysis with water, to the corresponding methylenic 1,4-diols 3 in a Barbier-type process. The cyclisation of diols 3 under acidic conditions (hydrochloric or phosphoric acid) yields the corresponding substituted methylenic tetrahydrofurans 4 . Finally, 2,3-dichloropropene ( 1 ) is converted into the corresponding allylic chloroamines 5 and then submitted to the tandem naphthalene-catalysed 2lithiation-S E reaction with different electrophiles affording the corresponding functionalised amines 7 . The last process fails for oxygen- or sulfur-containing chloroallylic materials 8 .