Tetrahedron Letters p. 1165 - 1168 (1982)
Update date:2022-08-05
Topics:
Tsushima, Tadahiko
Kawada, Kenji
Tsuji, Teruji
Xenon difluoride reacts smoothly with various steroid silyl enol ethers in the absence of any acid catalyst to afford stereoselectively α-oriented α-fluoroketones in good yields while iodotoluene difluoride reacts rather sluggishly with these silyl enol ethers to competitively produce β-oriented α-fluoro ketones, elimination and other nucleophilic substitution products.The observed stereochemical contrast clearly suggest an electrophilic and nucleophilic mechanism for these reactions, respectively.
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Doi:10.1007/BF00773817
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(1935)Doi:10.1055/s-1982-29857
(1982)Doi:10.1002/anie.201507806
(2016)Doi:10.1002/anie.201602382
(2016)Doi:10.1016/0040-4039(96)00682-X
(1996)