Tetrahedron Letters p. 587 - 590 (1997)
Update date:2022-08-02
Topics:
Kamaya, Hiroshi
Sato, Masayuki
Kaneko, Chikara
Molecular fluorine efficiently reacts with α-hydroxymethylene carbonyl compounds to give α-fluoro-α-formyl compounds in a highly site-specific manner. The fluorinated compounds mostly isolated as their hemiacetals with methanol are readily deformylated just by treatment with weak bases affording α-monofluorinated carbonyl compounds. In this fluorination method, the hydroxymethylene group serves not only as a directing group but also as the activating group of carbonyl compounds for fluorination. By this method, a series of α-fluoro carbonyl compounds including esters was synthesized in high yields.
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(1997)