22508-64-1Relevant articles and documents
Total synthesis of the terpenoid buddledone A: 11-membered ring-closing metathesis
Cai, Zhengxin,Yongpruksa, Nattawut,Harmata, Michael
, p. 1661 - 1663 (2012)
The first total synthesis of buddledone A was accomplished in seven steps from methyl ethyl ketone (MEK). The key step in the sequence featured an 11-membered ring formation by ring-closing metathesis.
Acyloxyetherifications mediated by lead tetracarboxylates
Cottrell, Ian F.,Moloney, Mark G.,Smithies, Kirsty
, p. 1097 - 1099 (2009)
Lead(IV) tetracarboxylates are capable of reacting with unsaturated alcohols to give the products of cyclic acyloxyetherification, usually as a mixture of tetrahydro-2H-pyranyl and tetrahydrofuranyl compounds.
Regio- and Stereoselectivity of the Intramolecular C-H Insertion by Cyclopropylidenes Bearing a Remote Oxido Substituent
Harada, Toshiro,Yamaura, Yasunari,Oku, Akira
, p. 1715 - 1720 (1987)
(ω-Oxidoalkyl)cyclopropylidenes generated from (2,2-dibromo-1-methylcyclopropyl)-CH2-X-(CH2)n-OH (X=CH2 or O, n=1, 2) by the reaction with methyllithium underwent a regioselective intramolecular insertion into the C-H bond at the δ position to the carbenic carbon.The activation effect of the oxido substituent on the reactivity of C-H bonds is discussed on the basis of (1) the ratio of the insertion products to the rearrangement product allenyl alcohol, and (2) the endo stereoselectivity of the present insertion reactions.
Cu-Catalyzed C-H Allylation of Benzimidazoles with Allenes
Dong, Yaxi,Breit, Bernhard
supporting information, p. 6765 - 6769 (2021/09/11)
CuH-catalyzed intramolecular cyclization and intermolecular allylation of benzimidazoles with allenes have been described. The reaction proceeded smoothly with the catalytic system of Cu(OAc)2/Xantphos and catalytic amount of (MeO)2MeSiH. This protocol features mild reaction conditions and a good tolerance of substrates bearing electron-withdrawing, electron-donating, or electron-neutral groups. A new catalytic mechanism was proposed for this copper hydride catalytic system.
Gold(I)/Gold(III) Catalysis that Merges Oxidative Addition and π-Alkene Activation
Amgoune, Abderrahmane,Bourissou, Didier,Rigoulet, Mathilde,Thillaye du Boullay, Olivier
supporting information, p. 16625 - 16630 (2020/07/24)
Heteroarylation of alkenes with aryl iodides was efficiently achieved with a (MeDalphos)AuCl complex through AuI/AuIII catalysis. The possibility to combine oxidative addition of aryl iodides and π-activation of alkenes at gold is demonstrated for the first time. The reaction is robust and general (>30 examples including internal alkenes, 5-, 6-, and 7-membered rings). It is regioselective and leads exclusively to trans addition products. The (P,N) gold complex is most efficient with electron-rich aryl substrates, which are troublesome with alternative photoredox/oxidative approaches. In addition, it provides a very unusual switch in regioselectivity from 5-exo to 6-endo cyclization between the Z and E isomers of internal alkenols.
Hydrogenative Cyclopropanation and Hydrogenative Metathesis
Peil, Sebastian,Guthertz, Alexandre,Biberger, Tobias,Fürstner, Alois
supporting information, p. 8851 - 8856 (2019/05/28)
The unusual geminal hydrogenation of a propargyl alcohol derivative with [CpXRuCl] as the catalyst entails formation of pianostool ruthenium carbenes in the first place; these reactive intermediates can be intercepted with tethered alkenes to give either cyclopropanes or cyclic olefins as the result of a formal metathesis event. The course of the reaction is critically dependent on the substitution pattern of the alkene trap.
