565-63-9Relevant articles and documents
Sokolova,Nikonov
, (1970)
The Occurrence of Some Novel Diesters in Roman Camomile Oil
Thomas, Alan F.
, p. 2397 - 2400 (1981)
Three diols, 2-methylidene-1,3-propanediol, 2-methyl-1,3-propanediol and 1,3-butanediol, esterified on one hydroxyl group with isobutyric acid and on the other with angelic acid), have been isolated from Anthemis nobilis oil (Roman camomile) an synthesized.The presence of homologous esters is very probable.
Nikonov,Baranauskaite
, (1965)
Nabiev et al.
, (1978)
Yunusov et al.
, (1976)
Dienolates of Cycloalkenones and α,β-Unsaturated Esters Form Diels–Alder Adducts by a Michael/Michael-Tandem Reaction Rather Than in One Step
Loesche, Ann-Christine,Brückner, Reinhard
supporting information, p. 562 - 573 (2018/12/11)
α,β-Unsaturated esters and lithium 1,3-dien-2-olates are known to furnish bicyclic lithium enolates by anionic Diels–Alder reactions. However, in principle, the respective products might form not only in a single step but also in two consecutive – or “tandem” – Michael additions, the first of which occurs intermolecularly, the second intramolecularly. Three cyclic lithium dienolates and four esters with a stereogenic Cα=Cβ bond reacted to give Diels–Alder adducts (10 times) or failed to react (2 times). Seven of the reactive combinations furnished adducts wherein the configuration of the former ester moiety had in part inverted. This precludes concerted pathways as their origins. This was a surprise since donors at C-2 of the 1,3-diene accelerate normal electron-demand Diels–Alder reactions in the order alkyl ⊕O? being a far better donor still, it is not obvious why the mechanism is non-concerted rather than concerted (and still more asynchronous).
Asymmetric dihydroxylation of esters and amides of methacrylic, tiglic, and angelic acid: No exception to the sharpless mnemonic!
Weber, Fabian,Brückner, Reinhard
, p. 2428 - 2449 (2015/04/22)
Literature findings on the facial selectivity of the Sharpless asymmetric dihydroxylation (SAD) of isobutyl angelate are contradictory and partly in conflict with the Sharpless mnemonic. We systematically screened the SAD of esters and amides of angelic, tiglic, and methacrylic acid. Enantiocontrol arose in 14 of the 15 reactions, culminating at 99 % ee for the Weinreb amide of tiglic acid. The absolute configurations of all the nonracemic products were established by (stereo)chemical correlations. Without exception, they conform to the Sharpless mnemonic.
