59627-41-7Relevant academic research and scientific papers
Borylation of propargylic substrates by bimetallic catalysis. Synthesis of allenyl, propargylic, and butadienyl bpin derivatives
Zhao, Tony S. N.,Yang, Yuzhu,Lessing, Timo,Szabó, Kálmán J.
supporting information, p. 7563 - 7566 (2014/06/10)
Bimetallic Pd/Cu and Pd/Ag catalytic systems were used for borylation of propargylic alcohol derivatives. The substrate scope includes even terminal alkynes. The reactions proceed stererospecifically with formal S N2′ pathways to give allenyl boronates. Opening of propargyl epoxides leads to 1,2-diborylated butadienes probably via en allenylboronate intermediate.
Combined rhodium/gold catalysis: From propargyloxiranes to 2,5-dihydrofurans in one pot
Aksin-Artok, Oezge,Krause, Norbert
supporting information; experimental part, p. 385 - 391 (2011/04/18)
A new and efficient one-pot synthesis of 2,5-dihydrofurans from propargyloxiranes and arylboronic acids takes advantage of sequential rhodium-gold catalysis. The transformation proceeds with center-to-axis-to- center chirality transfer and tolerates a wide variety of electron-accepting or electron-withdrawing substituents at the arylboronic acid, as well as cyclic or acyclic propargyloxiranes.
Stereoselective synthesis of syn-configured α-allenols by rhodium-catalyzed reaction of alkynyl oxiranes with arylboronic acids
Miura, Tomoya,Shimada, Masahiko,De Mendoza, Paula,Deutsch, Carl,Krause, Norbert,Murakami, Masahiro
supporting information; experimental part, p. 6050 - 6054 (2009/12/26)
(Chemical Equation Presented) A rhodium-catalyzed reaction of alkynyl oxiranes with arylboronic acids affords syn-configured α-allenols with high diastereoselectivity. The reaction is initiated by addition of an arylrhodium(I) species onto the alkyne moie
Diastereoselective syn or anti opening of propargylic epoxides. Synthesis of α-allenic alcohols
Alexakis,Marek,Mangeney,Normant
, p. 1677 - 1696 (2007/10/02)
Propargylic epoxides easily react with Grignard reagents and catalytic amounts of copper(I) salt to afford α-allenic alcohols. The reaction is highly diastereoselective and its stereochemical outcome (syn or anti isomer) can be fully controlled. The syn d
