Literature DB >> 21068369

Crystal structures of proline-derived enamines.

Dominique Anna Bock1, Christian W Lehmann, Benjamin List.   

Abstract

The isolation and structural characterization of both aldehyde- and ketone-derived proline enaminones are reported and discussed. Crystal structures of 10 proline enamines provide information on stereochemical aspects, i.e., double bond configuration and syn- vs. anti-positioning of the carboxylate relative to the enamine double bond. Furthermore, the obtained crystal structures are compared with the density functional theory-calculated structures of the ground and transition state and the postulated Seebach-Eschenmoser transition state.

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 21068369      PMCID： PMC2996454          DOI： 10.1073/pnas.1006509107

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  12 in total

1.  The origin of stereoselectivity in proline-catalyzed intramolecular aldol reactions.

Authors:  S Bahmanyar; K N Houk
Journal:  J Am Chem Soc       Date:  2001-12-26       Impact factor: 15.419

2.  Kinetic and stereochemical evidence for the involvement of only one proline molecule in the transition states of proline-catalyzed intra- and intermolecular aldol reactions.

Authors:  Linh Hoang; S Bahmanyar; K N Houk; Benjamin List
Journal:  J Am Chem Soc       Date:  2003-01-08       Impact factor: 15.419

3.  New mechanistic studies on the proline-catalyzed aldol reaction.

Authors:  Benjamin List; Linh Hoang; Harry J Martin
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-08       Impact factor: 11.205

4.  The elusive enamine intermediate in proline-catalyzed aldol reactions: NMR detection, formation pathway, and stabilization trends.

Authors:  Markus B Schmid; Kirsten Zeitler; Ruth M Gschwind
Journal:  Angew Chem Int Ed Engl       Date:  2010-07-05       Impact factor: 15.336

5.  Computational evidence for the enamine mechanism of intramolecular aldol reactions catalyzed by proline.

Authors:  Fernando R Clemente; K N Houk
Journal:  Angew Chem Int Ed Engl       Date:  2004-11-05       Impact factor: 15.336

6.  ESI-MS study on the aldol reaction catalyzed by L-proline.

Authors:  Cesar Marquez; Jürgen O Metzger
Journal:  Chem Commun (Camb)       Date:  2006-02-28       Impact factor: 6.222

Review 7.  Asymmetric enamine catalysis.

Authors:  Santanu Mukherjee; Jung Woon Yang; Sebastian Hoffmann; Benjamin List
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

8.  Transition states of amine-catalyzed aldol reactions involving enamine intermediates: theoretical studies of mechanism, reactivity, and stereoselectivity.

Authors:  S Bahmanyar; K N Houk
Journal:  J Am Chem Soc       Date:  2001-11-14       Impact factor: 15.419

9.  Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions.

Authors:  S Bahmanyar; K N Houk; Harry J Martin; Benjamin List
Journal:  J Am Chem Soc       Date:  2003-03-05       Impact factor: 15.419

10.  Enamine catalysis is a powerful strategy for the catalytic generation and use of carbanion equivalents.

Authors:  Benjamin List
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384
View more
  11 in total

1.  Organocatalysis.

Authors:  Eric N Jacobsen; David W C MacMillan
Journal:  Proc Natl Acad Sci U S A       Date:  2010-11-30       Impact factor: 11.205

2.  Stable, crystalline, porous, covalent organic frameworks as a platform for chiral organocatalysts.

Authors:  Hong Xu; Jia Gao; Donglin Jiang
Journal:  Nat Chem       Date:  2015-09-21       Impact factor: 24.427

3.  DFT study of the dual catalytic role of L-proline in the aldol reaction and the effect of water on it.

Authors:  Yasaman Nobakht; Nematollah Arshadi
Journal:  J Mol Model       Date:  2018-11-06       Impact factor: 1.810

4.  Developing novel organocatalyzed aldol reactions for the enantioselective synthesis of biologically active molecules.

Authors:  Mayur Bhanushali; Cong-Gui Zhao
Journal:  Synthesis (Stuttg)       Date:  2011-06       Impact factor: 3.157

5.  Stereoselectivities of histidine-catalyzed asymmetric aldol additions and contrasts with proline catalysis: a quantum mechanical analysis.

Authors:  Yu-hong Lam; K N Houk; Ulf Scheffler; Rainer Mahrwald
Journal:  J Am Chem Soc       Date:  2012-03-29       Impact factor: 15.419

6.  Catalysis of Hydrogen-Deuterium Exchange Reactions by 4-Substituted Proline Derivatives.

Authors:  Eddie L Myers; Michael J Palte; Ronald T Raines
Journal:  J Org Chem       Date:  2019-01-14       Impact factor: 4.354

7.  Proline editing: a general and practical approach to the synthesis of functionally and structurally diverse peptides. Analysis of steric versus stereoelectronic effects of 4-substituted prolines on conformation within peptides.

Authors:  Anil K Pandey; Devan Naduthambi; Krista M Thomas; Neal J Zondlo
Journal:  J Am Chem Soc       Date:  2013-03-11       Impact factor: 15.419

8.  Enamine/Dienamine and Brønsted Acid Catalysis: Elusive Intermediates, Reaction Mechanisms, and Stereoinduction Modes Based on in Situ NMR Spectroscopy and Computational Studies.

Authors:  Polyssena Renzi; Johnny Hioe; Ruth M Gschwind
Journal:  Acc Chem Res       Date:  2017-11-27       Impact factor: 22.384

Review 9.  The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research.

Authors:  James B McAlpine; Shao-Nong Chen; Andrei Kutateladze; John B MacMillan; Giovanni Appendino; Andersson Barison; Mehdi A Beniddir; Maique W Biavatti; Stefan Bluml; Asmaa Boufridi; Mark S Butler; Robert J Capon; Young H Choi; David Coppage; Phillip Crews; Michael T Crimmins; Marie Csete; Pradeep Dewapriya; Joseph M Egan; Mary J Garson; Grégory Genta-Jouve; William H Gerwick; Harald Gross; Mary Kay Harper; Precilia Hermanto; James M Hook; Luke Hunter; Damien Jeannerat; Nai-Yun Ji; Tyler A Johnson; David G I Kingston; Hiroyuki Koshino; Hsiau-Wei Lee; Guy Lewin; Jie Li; Roger G Linington; Miaomiao Liu; Kerry L McPhail; Tadeusz F Molinski; Bradley S Moore; Joo-Won Nam; Ram P Neupane; Matthias Niemitz; Jean-Marc Nuzillard; Nicholas H Oberlies; Fernanda M M Ocampos; Guohui Pan; Ronald J Quinn; D Sai Reddy; Jean-Hugues Renault; José Rivera-Chávez; Wolfgang Robien; Carla M Saunders; Thomas J Schmidt; Christoph Seger; Ben Shen; Christoph Steinbeck; Hermann Stuppner; Sonja Sturm; Orazio Taglialatela-Scafati; Dean J Tantillo; Robert Verpoorte; Bin-Gui Wang; Craig M Williams; Philip G Williams; Julien Wist; Jian-Min Yue; Chen Zhang; Zhengren Xu; Charlotte Simmler; David C Lankin; Jonathan Bisson; Guido F Pauli
Journal:  Nat Prod Rep       Date:  2018-07-13       Impact factor: 13.423

10.  (2S,4R)-4-hydroxyproline(4-nitrobenzoate): strong induction of stereoelectronic effects via a readily synthesized proline derivative. Crystallographic observation of a correlation between torsion angle and bond length in a hyperconjugative interaction.

Authors:  Anil K Pandey; Glenn P A Yap; Neal J Zondlo
Journal:  J Org Chem       Date:  2014-04-18       Impact factor: 4.354
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.