25091-25-2Relevant academic research and scientific papers
Dialkylaluminum hydride-promoted cyclodimerization of silylated 1,3-enynes via skeletal rearrangement
Kinoshita, Hidenori,Ishikawa, Tomoyuki,Miura, Katsukiyo
supporting information; experimental part, p. 6192 - 6195 (2012/01/06)
The dialkylaluminum hydride-promoted reaction of 1-silylalk-3-en-1-ynes gave symmetrical 1,2,3,5-tetrasubstituted benzenes as single regioisomers. The novel cyclodimerization via skeletal rearrangement can be rationalized by an unprecedented mechanism inv
Silaborations of 1,3-enynes - Substrate controlled allene/1,3-diene selectivity
Lueken, Christian,Moberg, Christina
supporting information; experimental part, p. 2505 - 2508 (2009/05/26)
(Chemical Equation Presented) Silaboration of 1,3-enynes catalyzed by group 10 metal complexes affords 1,3-dienes with vinylborane and vinylsilane functions or 1,2-dienes with allylborane and vinylsilane functions. The type of product formed is determined
Silver-catalyzed hydroamination of siloxy alkynes
Sun, Jianwei,Kozmin, Sergey A.
, p. 4991 - 4993 (2007/10/03)
(Chemical Equation Presented) New catalytic process: The silver-catalyzed hydroamination of siloxy alkynes with secondary amides furnishes silyl ketene aminals with high efficiency and excellent diastereoselectivity (see scheme), including some that are unavailable by conventional silylation methods. The reaction comprises a fast and reversible silver-alkyne complexation, followed by a rate-determining C-N bond-forming step.
Insertion of 1-chloro-1-lithioalkenes into organozirconocenes. A versatile synthesis of stereodefined unsaturated systems
Kasatkin, Aleksandr,Whitby, Richard J.
, p. 7039 - 7049 (2007/10/03)
Hydrozirconation of alkenes and alkynes, followed by insertion of 1- halo-1-lithio-1-alkenes, generated in situ by lithium tetramethylpiperidide deprotonation of vinyl halides, affords vinylzirconocene species which may be further elaborated. The method provides easy access to many structures including terminal (3E)- and (3Z)-1,3-dienes and (3E,5E)- and (3Z,5E)-1,3,5- trienes, and internal (E,Z)-dienes,(E,Z,E)-trienes, and (1E, 3Z)1,3-dien-5- ynes. Insertion of 2-monosubstituted 1-halo-1-lithio-1-alkenes occurs with clean inversion of configuration of the sp2-carbenoid carbon. Carbenoids derived by deprotonation of 2,2-disubstituted 1-halo-1-alkenes gave poor stereocontrol probably due to isomerization before insertion into the organozirconium species. Insertion of vinyl carbenoids into alkynylzirconocenes affords terminal (3E)- or (3Z)-1,3-dien-5-ynes, internal (1E,3Z)-1,3-dien-5-ynes, and (Z)-3-en-1,5-diynes.
