83816-45-9Relevant academic research and scientific papers
Asymmetric indium-mediated synthesis of homopropargylic alcohols
Hirayama, Lacie C.,Dunham, Kevin K.,Singaram, Bakthan
, p. 5173 - 5176 (2006)
A method for the enantioselective synthesis of homopropargylic alcohols using indium under Barbier-like conditions is reported herein. Both aromatic and aliphatic aldehydes were successfully converted to the corresponding homopropargylic alcohols in good
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
A facile lipase-catalyzed KR approach toward enantiomerically enriched homopropargyl alcohols
Borowiecki, Pawe?,Dranka, Maciej
, (2019/02/14)
Compounds possessing propargylic (prop-2-ynylic) system are very important building blocks for organic chemistry. Among them, preparation of enantiomeric homopropargyl alcohols (but-3-yn-1-ols) constitutes a key-challenge for asymmetric synthesis and thus
Enantioselective Allyl-, and Allenylboration of Aldehydes Catalyzed by Chiral Hydroxyl Carboxylic Acid
Ota, Yuya,Kawato, Yuji,Egami, Hiromichi,Hamashima, Yoshitaka
supporting information, p. 976 - 980 (2017/05/05)
Asymmetric allylboration of aldehydes with allylboronic acid pinacol ester catalyzed by chiral hydroxyl carboxylic acid is described. This reaction provides synthetically useful homoallyl alcohols in high yield with good to high enantioselectivity. The pr
Br?nsted acid-catalyzed asymmetric allylation and propargylation of aldehydes
-
Page/Page column 11, (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
Direct synthesis of B-allyl and B-allenyldiisopinocampheylborane reagents using allyl or propargyl halides and indium metal under Barbier-type conditions
Hirayama, Lacie C.,Haddad, Terra D.,Oliver, Allen G.,Singaram, Bakthan
supporting information; experimental part, p. 4342 - 4353 (2012/06/30)
We report the first one-pot process for the asymmetric addition of allyl, methallyl, and propargyl groups to aldehydes and ketones using B-chlorodiisopinocampheylborane (dDIP-Cl) and indium metal. Under Barbier-type conditions, indium metal was
Indium-mediated asymmetric Barbier-type propargylations: Additions to aldehydes and ketones and mechanistic investigation of the organoindium reagents
Haddad, Terra D.,Hirayama, Lacie C.,Buckley, Jannise J.,Singaram, Bakthan
experimental part, p. 889 - 898 (2012/03/11)
We report a simple, efficient, and general method for the indium-mediated enantioselective propargylation of aromatic and aliphatic aldehydes under Barbier-type conditions in a one-pot synthesis affording the corresponding chiral alcohol products in very
Highly potent macrocyclic BACE-1 inhibitors incorporating a hydroxyethylamine core: Design, synthesis and X-ray crystal structures of enzyme inhibitor complexes
Sandgren, Veronica,Agback, Tatiana,Johansson, Per-Ola,Lindberg, Jimmy,Kvarnstr?m, Ingemar,Samuelsson, Bertil,Belda, Oscar,Dahlgren, Anders
experimental part, p. 4377 - 4389 (2012/08/28)
A series of P1-P3 linked macrocyclic BACE-1 inhibitors containing a hydroxyethylamine (HEA) isostere scaffold has been synthesized. All inhibitors comprise a toluene or N-phenylmethanesulfonamide P2 moiety. Excellent BACE-1 potencies, both in enzymatic an
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
