139518-33-5Relevant academic research and scientific papers
Hydrogen borrowing catalysis using 1° and 2° alcohols: Investigation and scope leading to α and β branched products
Frost, James R.,Cheong, Choon Boon,Akhtar, Wasim M.,Caputo, Dimitri F.J.,Christensen, Kirsten E.,Stevenson, Neil G.,Donohoe, Timothy J.
supporting information, (2021/04/07)
The alkylation of a variety of ketones using 1° or 2° alcohols under hydrogen borrowing catalysis is described. Initial research focused on the α-alkylation of cyclopropyl ketones with higher 1° alcohols (i.e. larger than MeOH), leading to the formation of α-branched products. Our search for additional substrates with which to explore this chemistry led us to discover that di-ortho-substituted aryl ketones were also privileged scaffolds, with Ph? (C6Me5) ketones being the optimal choice. Further investigations revealed that this motif was crucial for alkylation with 2° alcohols forming β-branched products, which also provided an opportunity to study diastereoselective and intramolecular hydrogen borrowing processes.
Direct metalation of methoxymethyl arylmethyl ethers: A tin-free approach to the generation of α-alkoxyalkoxy-substituted aryllithiums
Azzena, Ugo,Pisano, Luisa,Mocci, Sarah
scheme or table, p. 3619 - 3625 (2010/01/18)
The generation of a series of α-methoxymethoxy-substituted arylmethyllithiums was achieved by direct metalation of the corresponding arylmethyl methoxymethyl ethers. While the effect of substituents at the benzylic position is straightforward, substituent
A new strategy for the stereoselective synthesis of 2,2′-bipyrrolidines
Gresser, Mary J.,Keller, Paul A.,Wales, Steven M.
scheme or table, p. 4899 - 4902 (2009/12/05)
A new strategy for the stereoselective synthesis of the 2,2′-bipyrrolidine scaffold is presented using a metathesis reaction followed by asymmetric dihydroxylation for the introduction of the stereogenic elements. This straightforward high-yielding process is suitable for application to the synthesis of additional heterocycles.
B(C6F5)3-catalyzed allylation of secondary benzyl acetates with allylsilanes
Rubin, Michael,Gevorgyan, Vladimir
, p. 2705 - 2707 (2007/10/03)
(Equation presented) A highly effective protocol for allylation of secondary benzylic alcohol derivatives with allylsilanes in the presence of catalytic amounts of B(C6F5)3 has been developed. Some additional functionalities, such as bromo, acetoxy, and primary benzyloxy groups, were tolerated under these conditions.
