Tetrahedron p. 4117 - 4126 (1993)
Update date:2022-08-05
Topics:
Gomez, Cecilia
Ramon, Diego J.
Yus, Miguel
The reaction of 3-chloro-2-chloromethylpropene (1) and carbonyl compounds (2) with an excess of lithium powder in the presence of a catalytic amount of naphthalene (6%) in tetrahydrofuran at -78 to 20°C leads, after hydrolysis, to the corresponding methylenic 1,5-diols 3 in a Barbier-type process. The treatment of the crude diols 3 with 12 M. hydrochloric acid affords selectively the corresponding substituted dihydropyrans 6.
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