91200-22-5Relevant academic research and scientific papers
Questioning the γ-gauche effect: Stereoassignment of 1,3-disubstituted-tetrahydro-β-carbolines using 1H-1H coupling constants
Caga?ová, Kristyna,Ghavami, Maryam,Yao, Zhong-Ke,Carlier, Paul R.
, p. 6687 - 6698 (2019/07/16)
The Pictet-Spengler reaction of tryptophan esters and aldehydes has been widely applied in natural product synthesis and medicinal chemistry. To date, the trans- or cis-configuration of 1,3-disubstituted tetrahydro-β-carbolines (THβCs) formed in this reac
Unexpected cis selectivity in the Pictet-Spengler reaction
Bailey, Patrick D.,Beard, Mark A.,Phillips, Theresa R.
experimental part, p. 3645 - 3647 (2009/09/30)
Whilst cis:trans selectivity of about 4:1 can be obtained from Pictet-Spengler reactions between tryptophan methyl esters and aldehydes using conditions of kinetic control, much higher cis selectivity (>95:5) can be obtained when both the tryptophan deriv
Syntheses of tetrahydro-β-carbolines via a tandem hydroformylation- Pictet-Spengler reaction. Scope and limitations
Bondzic, Bojan P.,Eilbracht, Peter
supporting information; experimental part, p. 4059 - 4063 (2009/06/27)
A novel one-pot synthesis of tetrahydro-β-carboline systems via tandem hydroformylation-Pictet-Spengler reaction starting from olefins and aryl ethylamines is described. This tandem procedure allows fast and convenient synthesis of various substituted tetrahydro-β-carbolines. The 2008 Royal Society of Chemistry.
Liquid-phase parallel synthesis of tetrahydro-β-carbolines
Yeh, Wen-Ben,Lin, Mei-Jung,Sun, Chung-Ming
, p. 4923 - 4926 (2007/10/03)
Parallel synthesis of β-carbolines on soluble polyethylene glycol (PEG-OH) support is demonstrated. One-pot condensation of polymer-bound tryptophan residues with various aldehydes and ketones has been carried out in the presence of p-TSA as a catalyst to deliver immobilized 1,2,3,4-tetrahydro-β-carbolines. Subsequent disengagement of the appendant from the polymer support afforded the desired products in good yield and acceptable purity.
Enhancing the Yield and Diastereoselectivity of the Pictet-Spengler Reaction: A Highly Efficient Route to Cis-1,3-Disubstituted Tetrahydro-β-Carbolines
Balley, Patrick D.,Moore, Madeleine H.,Morgan, Keith M.,Smith, David I.,Vernon, John M.
, p. 3587 - 3588 (2007/10/02)
Under conditions of kinetic control, the cis-diastereoselectivity of the Pictet-Spengler reaction between tryptophan esters and aldehydes can be controlled by varying the size of the ester group; the reaction proceeds in essentially quantitative yield wit
Diastereo- and Enantio-selectivity in the Pictet-Spengler Reaction
Bailey, Patrick D.,Hollinshead, Sean P.,McLay, Neil R.,Morgan, Keith,Palmer, Sarah J.,et al.
, p. 431 - 440 (2007/10/02)
The factors that control the relative and absolute stereochemistry of 1,3-disubstituted and 1,2,3-trisubstituted tetrahydro-β-carbolines formed via the Pictet-Spengler reaction are discussed.In particular, the stereochemical factors that lead to the predominance of cis-1,3-disubstituted products under conditions of kinetic control are presented, whith the aid of X-ray crystallographic data on a number of compounds; methods for assigning relative stereochemistry on the basis of NMR data are given; the mechanism by which racemisation can occur during the Pictet-Spengler reaction has also been studied, and procedures for eliminating this problem are given.
THE USE OF 13C N.M.R. IN THE DETERMINATION OF STEREOCHEMISTRY OF 1,2,3-TRISUBSTITUTED TETRAHYDRO-β-CARBOLINES
Bailey, Patrick D.,Hollinshead, Sean P.
, p. 389 - 399 (2007/10/02)
The chemical shift of the benzylic carbon of N(2)-benzyl-cis-1,3-disubstituted 1,2,3,4-tetrahydro-β-carbolines is downfield of the corresponding peak of the trans-isomer, and should be valuable, therefore, in the assignment of stereochemistry to these systems.
