Literature DB >> 18336025

Lithium enolates of simple ketones: structure determination using the method of continuous variation.

Lara R Liou1, Anne J McNeil, Antonio Ramirez, Gilman E S Toombes, Jocelyn M Gruver, David B Collum.   

Abstract

The method of continuous variation in conjunction with 6Li NMR spectroscopy was used to characterize lithium enolates derived from 1-indanone, cyclohexanone, and cyclopentanone in solution. The strategy relies on forming ensembles of homo- and heteroaggregated enolates. The enolates form exclusively chelated dimers in N,N,N',N'-tetramethylethylenediamine and cubic tetramers in tetrahydrofuran and 1,2-dimethoxyethane.

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Year:  2008        PMID： 18336025      PMCID： PMC2636850          DOI： 10.1021/ja7100642

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


  33 in total

1.  6Li and (15)N NMR Data as a Probe for the Influence of Solvent and Intramolecular Solvation on the Solution-State Structures of Chiral Lithium Amides The authors are most grateful to the Swedish Natural Science Research Council and Carl Trygger for financial support.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-04       Impact factor: 15.336

2.  Lithium and Cesium Ion-Pair Acidities of Dibenzyl Ketone. Aggregation of Lithium and Cesium Ion Pairs of the Enolate Ion and Dianion(1)(,).

Authors:  Roustam Gareyev; James C. Ciula; Andrew Streitwieser
Journal:  J Org Chem       Date:  1996-07-12       Impact factor: 4.354

3.  The regioselectivity of addition of organolithium reagents to enones and enals: the role of HMPA.

Authors:  W H Sikorski; H J Reich
Journal:  J Am Chem Soc       Date:  2001-07-11       Impact factor: 15.419

4.  Experimental evidence for chair-like transition states in aldol reactions of methyl ketone lithium enolates: stereoselective synthesis and utilization of a deuterium-labeled enolate as a probe of reaction stereochemistry.

Authors:  Christopher M Liu; William J Smith; Darin J Gustin; William R Roush
Journal:  J Am Chem Soc       Date:  2005-04-27       Impact factor: 15.419

5.  Structure and reactivity of mixed alkali metal alkoxide/aryloxide catalysts.

Authors:  R M Kissling; M R Gagné
Journal:  J Org Chem       Date:  2001-12-28       Impact factor: 4.354

6.  Determination of binding stoichiometry by the continuous variation method: the Job plot.

Authors:  C Y Huang
Journal:  Methods Enzymol       Date:  1982       Impact factor: 1.600

Review 7.  Lithium diisopropylamide: solution kinetics and implications for organic synthesis.

Authors:  David B Collum; Anne J McNeil; Antonio Ramirez
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 8.  Modern aldol methods for the total synthesis of polyketides.

Authors:  Bernd Schetter; Rainer Mahrwald
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-20       Impact factor: 15.336

9.  Characterization of beta-amino ester enolates as hexamers via 6Li NMR spectroscopy.

Authors:  Anne J McNeil; Gilman E S Toombes; Sithamalli V Chandramouli; Benoit J Vanasse; Timothy A Ayers; Michael K O'Brien; Emil Lobkovsky; Sol M Gruner; John A Marohn; David B Collum
Journal:  J Am Chem Soc       Date:  2004-05-19       Impact factor: 15.419

10.  Reaction of ketones with lithium hexamethyldisilazide: competitive enolizations and 1,2-additions.

Authors:  Pinjing Zhao; Anthony Condo; Ivan Keresztes; David B Collum
Journal:  J Am Chem Soc       Date:  2004-03-17       Impact factor: 15.419
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  24 in total

1.  From bifunctional to trifunctional (tricomponent nucleophile-transition metal-lewis acid) catalysis: the catalytic, enantioselective α-fluorination of acid chlorides.

Authors:  Jeremy Erb; Daniel H Paull; Travis Dudding; Lee Belding; Thomas Lectka
Journal:  J Am Chem Soc       Date:  2011-04-22       Impact factor: 15.419

2.  Disodium Salts of Pseudoephedrine-Derived Myers Enolates: Stereoselectivity and Mechanism of Alkylation.

Authors:  Yuhui Zhou; Ivan Keresztes; Samantha N MacMillan; David B Collum
Journal:  J Am Chem Soc       Date:  2019-10-15       Impact factor: 15.419

3.  On the nature of the oxidative heterocoupling of lithium enolates.

Authors:  Brian M Casey; Robert A Flowers
Journal:  J Am Chem Soc       Date:  2011-07-08       Impact factor: 15.419

4.  Structure determination using the method of continuous variation: lithium phenolates solvated by protic and dipolar aprotic ligands.

Authors:  Laura L Tomasevich; David B Collum
Journal:  J Org Chem       Date:  2013-07-15       Impact factor: 4.354

5.  Evans Enolates: Solution Structures of Lithiated Oxazolidinone-Derived Enolates.

Authors:  Evan H Tallmadge; David B Collum
Journal:  J Am Chem Soc       Date:  2015-10-05       Impact factor: 15.419

6.  Lithium Hexamethyldisilazide-Mediated Enolization of Highly Substituted Aryl Ketones: Structural and Mechanistic Basis of the E/Z Selectivities.

Authors:  Kyle A Mack; Andrew McClory; Haiming Zhang; Francis Gosselin; David B Collum
Journal:  J Am Chem Soc       Date:  2017-08-23       Impact factor: 15.419

7.  Solution structures of lithium enolates, phenolates, carboxylates, and alkoxides in the presence of N,N,N',N'-tetramethylethylenediamine: a prevalence of cyclic dimers.

Authors:  Jocelyn M Gruver; Lara R Liou; Anne J McNeil; Antonio Ramirez; David B Collum
Journal:  J Org Chem       Date:  2008-09-10       Impact factor: 4.354

8.  Lithium phenolates solvated by tetrahydrofuran and 1,2-dimethoxyethane: structure determination using the method of continuous variation.

Authors:  Timothy S De Vries; Anandarup Goswami; Lara R Liou; Jocelyn M Gruver; Emily Jayne; David B Collum
Journal:  J Am Chem Soc       Date:  2009-09-16       Impact factor: 15.419

9.  Structures of beta-amino ester enolates: new strategies using the method of continuous variation.

Authors:  Lara R Liou; Anne J McNeil; Gilman E S Toombes; David B Collum
Journal:  J Am Chem Soc       Date:  2008-12-24       Impact factor: 15.419

10.  Lithium Amino Alkoxide-Evans Enolate Mixed Aggregates: Aldol Addition with Matched and Mismatched Stereocontrol.

Authors:  Janis Jermaks; Evan H Tallmadge; Ivan Keresztes; David B Collum
Journal:  J Am Chem Soc       Date:  2018-02-19       Impact factor: 15.419
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