7766-51-0Relevant articles and documents
The electrophilic cleavage of cyclopropylcarbinylstannanes. Confirmation of Traylor's prediction
Lucke,Young
, p. 807 - 810 (1991)
The reaction of cyclopropylcarbinyltrialkylstannanes (CPCSnR3) 1a (R = Me) and 1b (R = Bu) with sulfur dioxide in chloroform or methanol yields the homoallylic tin sulphinates 2a and 2b respectively. The reaction of 1a with iodine in chloroform yields predominantly 4-iodo-1-butene (3) and trimethyltin iodide while in methanol the corresponding reaction yields CPCSnMe2I (4) and methyl iodide.
Cobalt-Catalyzed Regioselective Olefin Isomerization under Kinetic Control
Liu, Xufang,Zhang, Wei,Wang, Yujie,Zhang, Ze-Xin,Jiao, Lei,Liu, Qiang
supporting information, p. 6873 - 6882 (2018/05/30)
Olefin isomerization is a significant transformation in organic synthesis, which provides a convenient synthetic route for internal olefins and remote functionalization processes. The selectivity of an olefin isomerization process is often thermodynamically controlled. Thus, to achieve selectivity under kinetic control is very challenging. Herein, we report a novel cobalt-catalyzed regioselective olefin isomerization reaction. By taking the advantage of fine-tunable NNP-pincer ligand structures, this catalytic system features high kinetic control of regioselectivity. This mild catalytic system enables the isomerization of 1,1-disubstituted olefins bearing a wide range of functional groups in excellent yields and regioselectivity. The synthetic utility of this transformation was highlighted by the highly selective preparation of a key intermediate for the total synthesis of minfiensine. Moreover, a new strategy was developed to realize the selective monoisomerization of 1-alkenes to 2-alkenes dictated by installing substituents on the γ-position of the double bonds. Mechanistic studies supported that the in situ generated Co-H species underwent migratory insertion of double bond/β-H elimination sequence to afford the isomerization product. The less hindered olefin products were always preferred in this cobalt-catalyzed olefin isomerization due to an effective ligand control of the regioselectivity for the β-H elimination step.
Direct Generation of Triketide Stereopolyads via Merged Redox-Construction Events: Total Synthesis of (+)-Zincophorin Methyl Ester
Kasun, Zachary A.,Gao, Xin,Lipinski, Radoslaw M.,Krische, Michael J.
supporting information, p. 8900 - 8903 (2015/08/03)
(+)-Zincophorin methyl ester is prepared in 13 steps (longest linear sequence). A bidirectional redox-triggered double anti-crotylation of 2-methyl-1,3-propane diol directly assembles the triketide stereopolyad spanning C4-C12, significantly enhancing step economy and enabling construction of (+)-zincophorin methyl ester in nearly half the steps previously required.
