36971-12-7Relevant articles and documents
Rhodium catalysed carbonylation of homoallylic alcohols to spiropyrans bearing quaternary centres
Kitsos-Rzychon, Beate,Eilbracht, Peter
, p. 10721 - 10732 (1998)
A convenient preparation of substituted-spiropyrans via rhodium catalysed hydroformylation of homoallylic alcohols, followed by a condensation sequence to form hemiacetals and 2,2,3,3-tetraalkyl-4[H]- pyrans, is described.
An organotrifluoroborate-based convergent total synthesis of the potent cancer cell growth inhibitory depsipeptides kitastatin and respirantin
Beveridge, Ramsay E.,Batey, Robert A.
supporting information, p. 2322 - 2325 (2014/05/20)
The total syntheses of the highly cytotoxic neo-antimycin macrocyclic depsipeptide natural products kitastatin and respirantin have been accomplished in a convergent manner using MNBA promoted esterifications and an efficient C- and N-terminus bis-deprote
Iron-catalyzed electrochemical allylation of carbonyl compounds by allylic acetates
Durandetti, Muriel,Meignein, Clotilde,Perichon, Jacques
, p. 3121 - 3124 (2007/10/03)
Homoallylic alcohols were synthesized from aldehydes or ketones and allylic acetates, using an electrochemical process catalyzed by iron complexes. We first studied the reactivity of allyl acetate, using N,N-dimethylformamide (DMF) or acetonitrile (AN) as solvent, FeBr2 as catalyst, and Fe as the sacrificial anode. Then we tested the regioreactivity of crotyl acetate and other allylic derivatives.
Allylation of carbonyl compounds by allylic acetates using a cobalt halide as catalyst
Gomes, Paulo,Gosmini, Corinne,Perichon, Jacques
, p. 1909 - 1915 (2007/10/03)
In acetonitrile as solvent and in the presence of a simple cobalt halide as catalyst, the reduction by zinc dust of a mixture of aldehydes or ketones and allylic acetates affords the corresponding homoallylic alcohols in good yields.
Indium mediated allylation and propargylation reactions of dimethyl acetals and ketals
Kwon, Jin Sun,Pae, Ae Nim,Choi, Kyung Il,Koh, Hun Yeong,Kim, Youseung,Cho, Yong Seo
, p. 1957 - 1959 (2007/10/03)
Indium mediated allylation and propargylation reactions of acetals and ketals with various allyl or propargyl bromides in aqueous media successfully provided the corresponding homoallylic or homopropargylic (and allenylic) alcohol, respectively, in moderate to good yields. Highly chemoselective allylation is also described. The ketal and aryl acetal could be selectively allylated over the aliphatic one in 80-84% yields.
Regio- and Stereochemistry on the Electrophilic Trapping of Allylic Samariums Generated by Reductive Cleavage of Allylic Ethers with (C5Me5)2Sm(thf)n
Takaki, Ken,Kusudo, Takeshi,Uebori, Shinya,Nishiyama, Tetsushi,Kamata, Tohru,Yokoyama, Masaki,Takehira, Katsuomi,Makioka, Yoshikazu,Fujiwara, Yuzo
, p. 4299 - 4304 (2007/10/03)
The C-O bond of allylic benzyl ethers was selectively cleaved with Cp*2Sm(thf)n to give allylic samarium complexes in good yields. Facility of their bond fission has been found to be comparable to that of the corresponding propargylic ethers intermolecularly, but lower intramolecularly. Regio-and stereochemistry on the electrophilic trapping of the allylic complexes thus generated remarkably depended on the nature of the electrophiles. They reacted with carbonyl compounds exclusively from the most substituted terminus of the allylic moieties to yield blanched homoallylic alcohols with anti diasteroselectivity. On the other hand, trapping with silyl chlorides produced linear allylic silanes. Here, a plausible mechanism to account for the difference is proposed.
Homoallylic Alcohols from Samarium Diiodide-mediated Coupling of Allylic Sulfones with Carbonyl Compounds
Clayden, Jonathan,Julia, Marc
, p. 2261 - 2262 (2007/10/02)
Reduction of allylic sulfones with samarium diiodide gives allylsamarium species which react in situ with carbonyl compounds, yielding homoallylic alcohols.
Samarium(II)-mediated reaction of allylic phosphate esters with carbonyl compounds: A new method for "Umpolung" of allylic phosphates
Araki, Shuki,Hatano, Masahiro,Ito, Hirokazu,Butsugan, Yasuo
, p. 329 - 336 (2007/10/02)
Allylic phosphates allylate ketones and aldehydes in the presence of samarium(II) iodide.The coupling proceeds with the preservation of the olefin geometry ever, regio- and stereoselectivity are not high.
Highly Selective Carbon-Carbon Bond Forming Reactions Mediated by Chromium(II) Reagents
Hiyama, Tamejiro,Okude, Yoshitaka,Kimura, Keizo,Nozaki, Hitosi
, p. 561 - 568 (2007/10/02)
A low valent chromium reagent is generated from chromium(III) chloride and a half mol of lithium aluminum hydride in tetrahydrofuran.The reagent behaves similarly to anhydrous chromium(II) chloride, which is commercially available, and reduces allylic halides to produce unisolable allylchromium species which add efficiently to aldehydes or ketones with high degree of stereo- and chemoselectivity.Particularly, high threo selectivity is observed in the reaction of aldehydes and 1-bromo-2-butene and is ascribed to a chair-like six-membered transition state.Simple reduction od allylic and benzylic halides produces biallyls and bibenzyls, while gem-dibromocyclopropanes afford the corresponding allenes in excellent yields.
