Synthesis p. 612 - 615 (1987)
Update date:2022-09-26
Topics:
Takeuchi, Ken'ichi
Kitagawa, Itsuko
Akiyama, Fumio
Shibata, Tadashi
Kato, Midori
Okamoto, Kunio
Acylation of bridgehead aldehydes with 1-adamantanecarbonyl cation generated from 1-adamantyl cation and carbon monoxide, or with benzoyl trifluoromethanesulfonate, in the presence of trifluoromethanesulfonic acid causes ring-expansion of the aldehydes by one carbon atom.Work-up of the reaction mixture with water affords a bridgehead alcohol containing the acyloxy group on the vicinal carbon, which on saponification gives a vicinal glycol in good overall yields.For example, bicyclo<2.2.1>heptane-1-carbaldehyde gives bicyclo<2.2.2>octane-1,2-diol which is not easily accessible by the other methods.
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Doi:10.1016/S0020-1693(00)90430-4
(1987)Doi:10.1002/adsc.200700543
(2008)Doi:10.1021/jo502293q
(2014)Doi:10.1016/j.inoche.2007.11.024
(2008)Doi:10.1007/s10895-010-0697-y
(2011)Doi:10.1002/anie.200804570
(2008)