Tetrahedron Letters p. 4017 - 4020 (1997)
Update date:2022-07-31
Topics:
Benbow, John W.
Katoch, Reeti
Martinez, Bonnie L.
Shetzline, Steven B.
Reaction of the trimethylsilyl (TMS) enol ethers 6 derived from the conjugate addition of oganocopper reagents to 3,4-dimethylcyclopentenone with dimethyl dioxirane (DMDO) leads to α-hydroxy ketones 7 with predominantly the syn-methyl orientation. Exposure of these systems to methanolic lead tetraacetate (Pb(OAc)4) delivers aldehydic esters 8 which are homologated to die desired E-dienes 9 using Yamamoto's allylic phosphine oxide reagent.
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Doi:10.1016/S0040-4039(97)00897-6
(1997)Doi:10.1007/s00706-019-02422-6
(2019)Doi:10.1246/bcsj.41.261
(1968)Doi:10.1021/ja00003a055
(1991)Doi:10.1002/jhet.5570340356
(1997)Doi:10.1016/S0040-4039(97)01083-6
(1997)
