1228600-99-4Relevant academic research and scientific papers
The development of the asymmetric Morita-Baylis-Hillman reaction catalyzed by chiral Bronsted acids
McDougal, Nolan T.,Trevellini, Whitney L.,Rodgen, Stacy A.,Kliman, Laura T.,Schaus, Scott E.
, p. 1231 - 1240 (2004)
This report describes the development of a chiral Bronsted acid-catalyzed asymmetric Morita-Baylis-Hillman (MBH) reaction of cyclohexenone with aldehydes. During the course of our studies on chiral Lewis acid-promoted MBH reactions, we discovered that chi
Novel phosphoramidite ligand, preparation method thereof and application thereof in asymmetric carbonylation reaction
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Paragraph 0044-0047; 0052-0055, (2021/09/29)
I Application of the asymmetric II carbonylating reaction strategy, and the synthetic problems of the hexahydropyrrolindole alkaloid and the dimeric cyclic amine alkaloid are effectively solved by using the monodentate chiral ligand to solve the problem of low enantioselectivity in the asymmetric domino Heck Heck and carbonylation reaction.
Synthesis and structural aspects of N-triflylphosphoramides and their calcium salts'highly acidic and effective Bronsted acids
Rueping, Magnus,Nachtsheim, Boris J.,Koenigs, Rene M.,Ieawsuwan, Winai
experimental part, p. 13116 - 13126 (2011/02/24)
Recently, 1,1′-bi-2-naphthol (BINOL)-based N-triflylphosphoramides emerged as a new class of potent Bronsted acid catalysts. In this paper we describe the efficient synthesis of various BINOL-based N- triflylphosphoramides and their calcium salts. Furthermore, X-ray crystal structure analysis combined with energy-dispersive X-ray spectroscopy (EDX) measurements confirmed that the synthesised chiral N-triflylphosphoramides are highly acidic metal-free catalysts. Freedom! The synthesis and structure determination of various 1,1′-bi-2-naphthol (BINOL)-based N-triflylphosphoramides and their corresponding calcium salts is presented. A simple acidic treatment of the calcium salts provides the metal-free Bronsted acids (see scheme; Tf=trifluoromethanesulfonyl).
Synthesis of BINOL derived phosphorodithioic acids as new chiral Br?nsted acids and an improved synthesis of 3,3′-disubstituted H8-BINOL derivatives
Pousse, Guillaume,Devineau, Alice,Dalla, Vincent,Humphreys, Luke,Lasne, Marie-Claire,Rouden, Jacques,Blanchet, Jér?me
experimental part, p. 10617 - 10622 (2010/01/16)
Original phosphorodithioic acid diesters were prepared according to an improved synthesis of 3,3′-disubstituted H8-BINOL derivatives. In preliminary experiments, these new Br?nsted acids were tested as organocatalysts in three reactions. They promoted the Nazarov cyclisation with mixed selectivities, the Mannich reaction with good enantioselectivity and they catalyzed efficiently the alkylation of N-acyliminium with enol silyl ether.
A convenient protocol for the synthesis of axially chiral Br?nsted acids
Bartoszek, Michael,Beller, Matthias,Deutsch, Jens,Klawonn, Markus,K?ckritz, Angela,Nemati, Navid,Pews-Davtyan, Anahit
, p. 1316 - 1322 (2008/09/17)
Partially hydrogenated binaphthol monophosphoric acids were prepared via an improved four-step sequence. It is demonstrated that typical protection and deprotection of the phenolic groups are dispensable. The vinyl-substituted derivative has been polymerized to give a novel polymerized organocatalyst.
Asymmetric Morita-Baylis-Hillman reactions catalyzed by chiral Bronsted acids
McDougal, Nolan T.,Schaus, Scott E.
, p. 12094 - 12095 (2007/10/03)
Chiral BINOL-derived Bronsted acids catalyze the enantioselective asymmetric Morita-Baylis-Hillman (MBH) reaction of cyclohexenone with aldehydes. The asymmetric MBH reaction requires 2-20 mol % of the chiral Bronsted acid 2e or 2f and triethylphosphine a
