355806-92-7Relevant academic research and scientific papers
Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones
Shi, Zhanglin,Shen, Chaoren,Dong, Kaiwu
, p. 18039 - 18042 (2021/11/16)
Palladium-catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed.
Bi(cyclopentyl)diol-Derived Boronates in Highly Enantioselective Chiral Phosphoric Acid-Catalyzed Allylation, Propargylation, and Crotylation of Aldehydes
Yuan, Jinping,Jain, Pankaj,Antilla, Jon C.
, p. 12988 - 13003 (2020/11/23)
In this study, we disclose the catalytic addition of bi(cyclopentyl)diol-derived boronates to aldehydes promoted by chiral phosphoric acids, allowing for the formation of enantioenriched homoallylic, propargylic, and crotylic alcohols (up to >99% enantiom
Optimization of Catalyst Structure for Asymmetric Propargylation of Aldehydes with Allenyltrichlorosilane
Vaganov, Vladimir Yu.,Fukazawa, Yasuaki,Kondratyev, Nikolay S.,Shipilovskikh, Sergei A.,Wheeler, Steven E.,Rubtsov, Aleksandr E.,Malkov, Andrei V.
supporting information, p. 5467 - 5474 (2020/10/19)
The design of catalysts for asymmetric propargylations remains a challenging task, with only a handful of methods providing access to enantioenriched homopropargylic alcohols. In this work, guided by previously reported computational predictions, a set of
Br?nsted acid-catalyzed asymmetric allylation and propargylation of aldehydes
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Page/Page column 12, (2013/08/28)
A method synthesizing homoallylic or homopropargylic alcohols was developed to react aldehydes with allyl boronates, such as allylboronic acid pinacol ester, or allenylborates in the presence of a catalytic amount of a chiral binaphthyl-derived chiral pho
Chiral Bronsted acid catalyzed enantioselective propargylation of aldehydes with allenylboronate
Reddy, Leleti Rajender
supporting information; experimental part, p. 1142 - 1145 (2012/03/27)
A highly enantioselective chiral Bronsted acid catalyzed propargylation of aldehydes with allenylboronate is described. The reaction is shown to be practical and quite general with a broad substrate scope covering aryl, polyaryl, heteroaryl, α,β-unsaturat
Enantioselective carbonyl propargylation by iridium-catalyzed transfer hydrogenative coupling of alcohols and propargyl chlorides
Woo, Sang Kook,Geary, Laina M.,Krische, Michael J.
, p. 7830 - 7834 (2012/09/07)
It takes alkynes! Exposure of propargyl chlorides to primary benzylic alcohols in the presence of [Ir(cod){(R)-segphos}]OTf (cod=1,5-cyclooctadiene, segphos=5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole, Tf=trifluoromethanesulfonyl) results in hydr
Bronsted acid catalyzed asymmetric propargylation of aldehydes
Jain, Pankaj,Wang, Hao,Houk, Kendall N.,Antilla, Jon C.
supporting information; experimental part, p. 1391 - 1394 (2012/03/11)
Which gets activated? A versatile and highly enantioselective chiral Bronsted acid catalyzed method for the propargylation of aldehydes is described to provide a range of chiral homopropargylic alcohols. Computational studies support the belief that the c
Ligand-accelerated enantioselective propargylation of aldehydes via allenylzinc reagents
Trost, Barry M.,Ngai, Ming-Yu,Dong, Guangbin
supporting information; experimental part, p. 1900 - 1903 (2011/06/21)
An enantioselective propargylation of aldehydes using an allenylzinc reagent generated in situ via a zinc-iodine exchange reaction is described. The enantioselectivity is controlled by addition of a catalytic amount of readily accessible and highly tunable amino alcohol ligand L13. A wide range of aldehydes can be propargylated to afford valuable and versatile homopropargyl alcohols in good to excellent yields with high levels of enantiopurity.
