Literature DB >> 20297822

The productive merger of iodonium salts and organocatalysis: a non-photolytic approach to the enantioselective alpha-trifluoromethylation of aldehydes.

Anna E Allen1, David W C Macmillan.   

Abstract

An enantioselective organocatalytic alpha-trifluoromethylation of aldehydes has been accomplished using a commercially available, electrophilic trifluoromethyl source. The merging of Lewis acid and organocatalysis provides a new strategy for the enantioselective construction of trifluoromethyl stereogenicity, an important chiral synthon for pharmaceutical, materials, and agrochemical applications. This mild and operationally simple protocol allows rapid access to enantioenriched alpha-trifluoromethylated aldehydes through a nonphotolytic pathway.

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Year:  2010        PMID： 20297822      PMCID： PMC2880471          DOI： 10.1021/ja100748y

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


  11 in total

1.  Electrophilic Perfluoroalkylating Agents.

Authors:  Teruo Umemoto
Journal:  Chem Rev       Date:  1996-08-01       Impact factor: 60.622

2.  Mild electrophilic trifluoromethylation of carbon- and sulfur-centered nucleophiles by a hypervalent iodine(III)-CF3 reagent.

Authors:  Iris Kieltsch; Patrick Eisenberger; Antonio Togni
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Novel 10-I-3 hypervalent iodine-based compounds for electrophilic trifluoromethylation.

Authors:  Patrick Eisenberger; Sebastian Gischig; Antonio Togni
Journal:  Chemistry       Date:  2006-03-08       Impact factor: 5.236

4.  Mild electrophilic trifluoromethylation of secondary and primary aryl- and alkylphosphines using hypervalent iodine(iii)-CF(3) reagents.

Authors:  Patrick Eisenberger; Iris Kieltsch; Nicolas Armanino; Antonio Togni
Journal:  Chem Commun (Camb)       Date:  2008-03-03       Impact factor: 6.222

5.  Enantioselective organocatalytic alpha-fluorination of aldehydes.

Authors:  Teresa D Beeson; David W C Macmillan
Journal:  J Am Chem Soc       Date:  2005-06-22       Impact factor: 15.419

6.  Direct and enantioselective organocatalytic alpha-chlorination of aldehydes.

Authors:  Michael P Brochu; Sean P Brown; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2004-04-07       Impact factor: 15.419

7.  Enantioselective electrophilic trifluoromethylation of beta-keto esters with Umemoto reagents induced by chiral nonracemic guanidines.

Authors:  Shun Noritake; Norio Shibata; Yoshinori Nomura; Yiyong Huang; Andrej Matsnev; Shuichi Nakamura; Takeshi Toru; Dominique Cahard
Journal:  Org Biomol Chem       Date:  2009-07-10       Impact factor: 3.876

Review 8.  Fluorine in medicinal chemistry.

Authors:  Sophie Purser; Peter R Moore; Steve Swallow; Véronique Gouverneur
Journal:  Chem Soc Rev       Date:  2007-12-13       Impact factor: 54.564

Review 9.  Fluorine in pharmaceuticals: looking beyond intuition.

Authors:  Klaus Müller; Christoph Faeh; François Diederich
Journal:  Science       Date:  2007-09-28       Impact factor: 47.728

10.  Enantioselective alpha-trifluoromethylation of aldehydes via photoredox organocatalysis.

Authors:  David A Nagib; Mark E Scott; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2009-08-12       Impact factor: 15.419
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  27 in total

1.  Synergistic palladium/enamine catalysis for asymmetric hydrocarbon functionalization of unactivated alkenes with ketones.

Authors:  Chiyu Wei; Xiaohan Ye; Qingyu Xing; Yong Hu; Yan Xie; Xiaodong Shi
Journal:  Org Biomol Chem       Date:  2019-06-25       Impact factor: 3.876

2.  Asymmetric oxidative dearomatizations promoted by hypervalent iodine(III) reagents: an opportunity for rational catalyst design?

Authors:  Andrew M Harned
Journal:  Tetrahedron Lett       Date:  2014-08-20       Impact factor: 2.415

Review 3.  Catalysis for fluorination and trifluoromethylation.

Authors:  Takeru Furuya; Adam S Kamlet; Tobias Ritter
Journal:  Nature       Date:  2011-05-26       Impact factor: 49.962

4.  Copper-catalyzed trifluoromethylation of unactivated olefins.

Authors:  Andrew T Parsons; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-25       Impact factor: 15.336

5.  Enantioselective α-vinylation of aldehydes via the synergistic combination of copper and amine catalysis.

Authors:  Eduardas Skucas; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2012-05-29       Impact factor: 15.419

6.  Photoredox catalysis: a mild, operationally simple approach to the synthesis of α-trifluoromethyl carbonyl compounds.

Authors:  Phong V Pham; David A Nagib; David W C MacMillan
Journal:  Angew Chem Int Ed Engl       Date:  2011-05-23       Impact factor: 15.336

7.  Enantioselective α-alkenylation of aldehydes with boronic acids via the synergistic combination of copper(II) and amine catalysis.

Authors:  Jason M Stevens; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2013-08-05       Impact factor: 15.419

8.  Photochemical Perfluoroalkylation with Pyridine N-Oxides: Mechanistic Insights and Performance on a Kilogram Scale.

Authors:  Joel W Beatty; James J Douglas; Richard Miller; Rory C McAtee; Kevin P Cole; Corey R J Stephenson
Journal:  Chem       Date:  2016-09-08       Impact factor: 22.804

9.  Enantioselective α-arylation of aldehydes via the productive merger of iodonium salts and organocatalysis.

Authors:  Anna E Allen; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2011-03-09       Impact factor: 15.419

10.  Simple catalytic mechanism for the direct coupling of α-carbonyls with functionalized amines: a one-step synthesis of Plavix.

Authors:  Ryan W Evans; Jason R Zbieg; Shaolin Zhu; Wei Li; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2013-10-16       Impact factor: 15.419
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