27749-07-1Relevant articles and documents
Organocuprate Conjugate Addition to 2,3-Dihydro-4H-pyran-4-ones
Boring, Daniel L.,Sindelar, Robert D.
, p. 3617 - 3621 (1988)
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A model study for the total synthesis of (±)-scopadulin: Stereoselective construction of the A/B ring system with desired functionalities
Abdur Rahman,Ohno, Hiroaki,Yoshino, Hitoshi,Satoh, Norifumi,Tsukaguchi, Mahoto,Murakami, Kazuo,Iwata, Chuzo,Maezaki, Naoyoshi,Tanaka, Tetsuaki
, p. 127 - 134 (2007/10/03)
A model study toward the total synthesis of (±)-scopadulin is described. Stereocontrolled synthesis of the A/B ring system with desired functionalities was achieved by stereoselective cyanation of a bicyclic enone with Et2AlCN, diastereoselective construction of a quaternary carbon at C-4 with LDA-BOMCl, and conversion of the cyano group into a methyl group.
The Role of BF3*Et2O in Reactions of Lower Order (Gilman) Organocuprates
Lipshutz, Bruce H.,Ellsworth, Edmund L.,Siahaan, Teruna J.
, p. 1351 - 1358 (2007/10/02)
The effects of BF3*Et2O on lower order organocuprate reactions in THF have been investigated so as to determine what factors are responsible for the oftentimes dramatic reaction-rate enhancements observed.From spectroscopic experiments on the reagents alone, supported further by chemical studies, it was found that an orginally formed cuprate (R2CuLi or RR'CuLi) is altered significantly upon exposure to this Lewis acid.The copper-containing species thereby generated, together with BF3, form a more reactive combination and appear to be at least in part responsible forthe accelerated chemistry.
