Literature DB >> 16536527

Origins of stereoselectivity in Diels-Alder cycloadditions catalyzed by chiral imidazolidinones.

Ruth Gordillo1, K N Houk.   

Abstract

B3LYP/6-31G(d) density functional theory has been used to study Diels-Alder reactions of cyclopentadiene with alpha,beta-unsaturated aldehydes and ketones organocatalyzed by MacMillan's chiral imidazolidinones. Preferred conformations of transition structures and reaction intermediates have been located. The dramatically different reactivities and enantioselectivities exhibited by two similar chiral imidazolidinones are rationalized.

Entities:  

Mesh：

Substances：

Year:  2006        PMID： 16536527      PMCID： PMC3164120          DOI： 10.1021/ja0525859

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  29 in total

1.  Molden: a pre- and post-processing program for molecular and electronic structures.

Authors:  G Schaftenaar; J H Noordik
Journal:  J Comput Aided Mol Des       Date:  2000-02       Impact factor: 3.686

2.  Enantioselective Organocatalysis.

Authors:  Peter I. Dalko; Lionel Moisan
Journal:  Angew Chem Int Ed Engl       Date:  2001-10-15       Impact factor: 15.336

3.  Kinetics study and theoretical modeling of the Diels-Alder reactions of cyclopentadiene and cyclohexadiene with methyl vinyl ketone. The effects of a novel organotungsten catalyst.

Authors:  Yaw-Shien Fu; Shih-Chung Tsai; Chun-Huei Huang; Shih-Yao Yen; Wei-Ping Hu; Shuchun Joyce Yu
Journal:  J Org Chem       Date:  2003-04-18       Impact factor: 4.354

4.  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

5.  A metal-free transfer hydrogenation: organocatalytic conjugate reduction of alpha,beta-unsaturated aldehydes.

Authors:  Jung Woon Yang; Maria T Hechavarria Fonseca; Benjamin List
Journal:  Angew Chem Int Ed Engl       Date:  2004-12-10       Impact factor: 15.336

6.  Origin of the synchronicity on the transition structures of polar Diels-Alder reactions. Are these reactions [4 + 2] processes?

Authors:  Luis R Domingo; M José Aurell; Patricia Pérez; Renato Contreras
Journal:  J Org Chem       Date:  2003-05-16       Impact factor: 4.354

7.  The role of steric and electronic interactions in the stereocontrol of the asymmetric 1,3-dipolar reactions of 5-ethoxy-3-p-(S)-tolylsulfinylfuran-2(5H)-ones with diazoalkanes: theoretical calculations and experimental evidences.

Authors:  José L García Ruano; Alberto Fraile; Gemma González; M Rosario Martín; Fernando R Clemente; Ruth Gordillo
Journal:  J Org Chem       Date:  2003-08-22       Impact factor: 4.354

8.  Organocatalytic asymmetric conjugate addition of nitroalkanes to alpha,beta-unsaturated enones using novel imidazoline catalysts.

Authors:  Nis Halland; Rita G Hazell; Karl Anker Jørgensen
Journal:  J Org Chem       Date:  2002-11-29       Impact factor: 4.354

9.  The first enantioselective organocatalytic Mukaiyama-Michael reaction: a direct method for the synthesis of enantioenriched gamma-butenolide architecture.

Authors:  Sean P Brown; Nicole C Goodwin; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2003-02-05       Impact factor: 15.419

10.  Origins of enantioselectivity in reductions of ketones on cinchona alkaloid modified platinum.

Authors:  Grigoriy Vayner; K N Houk; Y-K Sun
Journal:  J Am Chem Soc       Date:  2004-01-14       Impact factor: 15.419
View more
  6 in total

Review 1.  Quantum mechanical investigations of organocatalysis: mechanisms, reactivities, and selectivities.

Authors:  Paul Ha-Yeon Cheong; Claude Y Legault; Joann M Um; Nihan Çelebi-Ölçüm; K N Houk
Journal:  Chem Rev       Date:  2011-06-28       Impact factor: 60.622

Review 2.  The Cation-π Interaction in Small-Molecule Catalysis.

Authors:  C Rose Kennedy; Song Lin; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-22       Impact factor: 15.336

3.  Oxyanion steering and CH-π interactions as key elements in an N-heterocyclic carbene-catalyzed [4 + 2] cycloaddition.

Authors:  Scott E Allen; Jessada Mahatthananchai; Jeffrey W Bode; Marisa C Kozlowski
Journal:  J Am Chem Soc       Date:  2012-07-16       Impact factor: 15.419

4.  Entropic intermediates and hidden rate-limiting steps in seemingly concerted cycloadditions. Observation, prediction, and origin of an isotope effect on recrossing.

Authors:  Ollie M Gonzalez-James; Eugene E Kwan; Daniel A Singleton
Journal:  J Am Chem Soc       Date:  2012-01-18       Impact factor: 15.419

5.  Synthesis and antibacterial properties of (-)-nor-platencin.

Authors:  Olga V Barykina; Kerri L Rossi; Michael J Rybak; Barry B Snider
Journal:  Org Lett       Date:  2009-11-19       Impact factor: 6.005

6.  Origin of stereoselectivity in the imidazolidinone-catalyzed reductions of cyclic alpha,beta-unsaturated ketones.

Authors:  Osvaldo Gutierrez; Robert G Iafe; K N Houk
Journal:  Org Lett       Date:  2009-10-01       Impact factor: 6.005
  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.