125923-35-5Relevant academic research and scientific papers
An organocatalytic cascade strategy for the enantioselective construction of spirocyclopentane bioxindoles containing three contiguous stereocenters and two spiro quaternary centers
Sun, Wangsheng,Zhu, Gongming,Wu, Chongyang,Hong, Liang,Wang, Rui
, p. 6737 - 6741 (2012/07/28)
A rapid and efficient organocatalytic cascade sequence for the direct construction of spirocyclopentane bioxindoles has been carried out by using a chiral squaramide catalyst in the presence of a base. This process constitutes a powerful approach to the preparation of biologically important bispirooxindoles in high enantioselectivities (see scheme). Copyright
Conjugate addition - Dipolar cycloaddition cascade for the synthesis of benzo[a]quinolizine and indolo[a]quinolizine scaffolds: Application to the total synthesis of (±)-yohimbenone
Stearman, Chad J.,Wilson, Michael,Padwa, Albert
experimental part, p. 3491 - 3499 (2009/09/08)
A highly efficient total synthesis of (±)-yohimbenone and a formal synthesis of (±)-emetine is described. The key element of the synthesis consists of a conjugate addition-dipolar cycloaddition of 2,3- bis(phenylsulfonyl)-l,3-butadiene with an appropriate oxime. The resulting cycloadducts are cleaved reductively to provide azapolycyclic scaffolds with strategically placed functionality for further manipulation to the target compounds.
Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives
Suarez-Castillo, Oscar R.,Melendez-Rodriguez, Myriam,Castelan-Duarte, Luis Enrique,Sanchez-Zavala, Maricruz,Rivera-Becerril, Ernesto,Morales-Rios, Martha S.,Joseph-Nathan, Pedro
experimental part, p. 2374 - 2389 (2010/03/24)
We describe a reliable method for determining the absolute configuration of 2-(2-oxo-3-indolyl)acetamides based on analysis of the 1H NMR spectra of their phenylethylamide diastereomers. The conformational preferences for two diastereomeric ami
Intramolecular inverse electron demand Diels-Alder reactions of tryptamine with tethered heteroaromatic azadienes
Benson, Scott C.,Lee, Lily,Yang, Lydie,Snyder, John K.
, p. 1165 - 1180 (2007/10/03)
1,2,4,5-Tetrazines and 1,2,4-triazines tethered to tryptamine via the ethylamine side chain undergo intramolecular inverse electron demand cycloadditions to produce adducts with the [ABazaCE]-ring skeleton of the Aspidosperma alkaloids. (C) 2000 Elsevier Science Ltd.
REACTIONS OF β-KETO ESTERS WITH 2-CYANO-1,2,5,6-TETRAHYDROPYRIDINES
Chapman, R. F.,Phillips, N. I. J.,Ward, R. S.
, p. 5229 - 5234 (2007/10/02)
Reaction of the sodium salts of β-keto esters 13a and 13b with the 2-cyano-tetrahydropyridines 11 and 12 afforded the 4-substituted piperidine derivatives 21-23.The structures were assigned on the basic of their (1)H-and (13)C-NMR spectra and by comparison with the model compounds 24-26.The stereochemistry and the mechanism of the reactions are discussed.
