105575-91-5Relevant academic research and scientific papers
Polyfunctional Lithium, Magnesium, and Zinc Alkenyl Reagents as Building Blocks for the Synthesis of Complex Heterocycles
Shen, Zhi-Liang,Dhayalan, Vasudevan,Benischke, Andreas D.,Greiner, Robert,Karaghiosoff, Konstantin,Mayer, Peter,Knochel, Paul
, p. 5332 - 5336 (2016)
New conjunctive β-silylated organometallic reagents of Li, Mg, and Zn have been prepared and used for an expeditive construction of various polyfunctionalized 5-, 6-, and 7-membered heterocycles, such as furans, pyrroles, quinolines, benzo[b]thieno-[2,3-b
Anti-hydroalumination of homo- and bishomopropargyl alcohols
Ma, Shengming,Liu, Fang,Negishi, Ei-Ichi
, p. 3829 - 3832 (2007/10/03)
The reaction of ω-Me3Si- or ω-Me3Ge-substituted 3-butyn-1-ol, 4-pentyn-1-ol, and their derivatives with DIBAL-H and a small trialkylalane, e.g., Me3Al or Et3Al, at 23°C gives, after iodinolysis, the corresponding (Z)-4-iodo-3-buten-1-ols and (Z)-5-iodo-4-penten-1-ols in a highly stereo- and regio-selective manner, most probably via endo-dig mode cyclic anti-hydroalumination, while treatment of ω-carbosubstituted 3-butyn-1-ols with Red-Al or LialH4 at high temperatures followed by iodinolysis can give the corresponding (Z)-4-iodo-3-buten-1-ols also in a highly regio- and stereoselective manner.
Stereodefined Substituted Cyclopropyl Zinc Reagents from Gem-Bismetallics
Beruben, Dov,Marek, Ilane,Normant, Jean F.,Platzer, Nicole
, p. 2488 - 2501 (2007/10/02)
1,1- or n,n-Bismetallic reagents bearing a methoxymethyl ether in the γ position undergo cyclization at room temperature to give monometalated, diastereoselectively substituted cyclopropanes.The nature of the substituents is crucial for this diastereoselection, a ?-chelation between one metal and a properly located unsaturation, as well as 1,2-strain, are proposed to explain the steric outcome of these reactions.
A convenient procedure for the efficient preparation of alkyl (Z)-3-iodo-2-alkenoates
Piers, Edward,Wong, Timothy,Coish, Philip D.,Rogers, Christine
, p. 1816 - 1819 (2007/10/02)
Reaction of alkyl 2-alkynoates with sodium iodide (1.6-5.5 equiv.) in acetic acid (6.2-13 equiv.) at 115 deg C provides good to excellent yields of the corresponding alkyl (Z)-3-iodo-2-alkenoates.
Synthesis of Silicon Substituted Cyclopropylmethyl Alcohols in Optically Active Form via Asymmetric Simmons-Smith Reaction of γ-Silicon Substituted Allylic Alcohols
Ukaji, Yutaka,Sada, Kazunori,Inomata, Katsuhiko
, p. 1227 - 1230 (2007/10/02)
Optically active silicon substituted cyclopropyl methyl alcohols were synthesized through asymmetric Simmons-Smith reaction; that is, the reaction of γ-silicon substituted allylic alcohols with diethylzinc and diiodomethane utilizing (+)-diethyl tartrate
A NEW STEREOSELECTIVE SYNTHESIS OF (Z)-VINYLSILANE ALLYLIC ALCOHOLS
Kim, Kee D.,Magriotis, Plato A.
, p. 6137 - 6140 (2007/10/02)
A new, highly stereoselective method for the synthesis of (Z)-vinylsilane allylic alcohols 3 is described.This approach to such γ-silylated allylic alcohols employs a novel 1,4-O -> sp2C silyl rearrangement of appropriate silyl ether precursors
19. Silicon-Directed Nazarov Cyclizations Part V Substituent and Heteroatom Effects on the Reaction
Denmark, Scott E.,Habermas, Karl L.,Hite, Gary A.
, p. 168 - 194 (2007/10/02)
The ability to incorporate alkyl, alkenyl, aryl, and heteroatomic groups into substrates for the silicon-directed Nazarov cyclization and their subsequent reactions has been investigated.In general, most of the groups are compatible with the conditions for the cyclization and do not interfere even when directly attached to the divinyl ketone.The influence of substituents on the rate of the cyclization has been addressed and is consistent with a simple mechanistic picture.O- and N-containing functions are tolerated except when attached to the α-vinyl C-atom of the divinyl ketone.The diastereoface-directing effect of a fused cyclobutane is discussed.
