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Literature DB >> 18785744

Decarboxylative allylation using sulfones as surrogates of alkanes.

Abstract

Alpha-sulfonyl functional groups are traceless activating groups that facilitate catalytic decarboxylative allylations in high yield yet can be cleaved to allow the synthesis of simple allylated alkanes. Substrate studies suggest that decarboxylation to form an alpha-sulfonyl anion is rate-limiting. Furthermore, the anion is formed regiospecifically under formally neutral conditions.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2008 PMID： 18785744 PMCID： PMC2754783 DOI： 10.1021/ol801951e

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

10 in total

1. Solid-phase synthesis of 3,4-dihydro-1H-pyrimidine-2-ones using sodium benzenesulfinate as a traceless linker.

Authors: Weiwei Li; Yulin Lam
Journal: J Comb Chem Date: 2005 Sep-Oct

2. Synthesis of homoallylic sulfones through a decarboxylative claisen rearrangement reaction.

Authors: Damien Bourgeois; Donald Craig; N Paul King; David M Mountford
Journal: Angew Chem Int Ed Engl Date: 2005-01-14 Impact factor: 15.336

3. Deracemization of quaternary stereocenters by Pd-catalyzed enantioconvergent decarboxylative allylation of racemic beta-ketoesters.

Authors: Justin T Mohr; Douglas C Behenna; Andrew M Harned; Brian M Stoltz
Journal: Angew Chem Int Ed Engl Date: 2005-10-28 Impact factor: 15.336

4. Synthesis of homoallylic amines via the palladium-catalyzed decarboxylative coupling of amino acid derivatives.

Authors: Erin C Burger; Jon A Tunge
Journal: J Am Chem Soc Date: 2006-08-09 Impact factor: 15.419

5. Catalytic decarboxylative sp-sp3 coupling.

Authors: Dinesh Kumar Rayabarapu; Jon A Tunge
Journal: J Am Chem Soc Date: 2005-10-05 Impact factor: 15.419

6. Asymmetric allylic alkylation of cyclic vinylogous esters and thioesters by Pd-catalyzed decarboxylation of enol carbonate and beta-ketoester substrates.

Authors: Barry M Trost; Robert N Bream; Jiayi Xu
Journal: Angew Chem Int Ed Engl Date: 2006-05-05 Impact factor: 15.336

7. Decarboxylative Claisen rearrangement reactions of allylic tosylmalonate esters.

Authors: Donald Craig; Fabienne Grellepois
Journal: Org Lett Date: 2005-02-03 Impact factor: 6.005

8. A New Palladium-Catalyzed Intramolecular Allylation to Pyrrolidin-2-ones(1).

Authors: Giuliano Giambastiani; Barbara Pacini; Marina Porcelloni; Giovanni Poli
Journal: J Org Chem Date: 1998-02-06 Impact factor: 4.354

9. Asymmetric allylic alkylation of ketone enolates: an asymmetric Claisen surrogate.

Authors: Erin C Burger; Jon A Tunge
Journal: Org Lett Date: 2004-10-28 Impact factor: 6.005

10. Palladium-catalyzed decarboxylative sp3-sp3 coupling of nitrobenzene acetic esters.

Authors: Shelli R Waetzig; Jon A Tunge
Journal: J Am Chem Soc Date: 2007-11-08 Impact factor: 15.419

10 in total

11 in total

1. Deacylative allylation: allylic alkylation via retro-Claisen activation.

Authors: Alexander J Grenning; Jon A Tunge
Journal: J Am Chem Soc Date: 2011-08-24 Impact factor: 15.419

Review 2. Transition metal-catalyzed decarboxylative allylation and benzylation reactions.

Authors: Jimmie D Weaver; Antonio Recio; Alexander J Grenning; Jon A Tunge
Journal: Chem Rev Date: 2011-01-14 Impact factor: 60.622

3. Synthesis of Chiral Nonracemic Tertiary α-Thio and α-Sulfonyl Acetic Esters via S(N)2 reactions of Tertiary Mesylates.

Authors: Jimmie D Weaver; David K Morris; Jon A Tunge
Journal: Synlett Date: 2010-02-01 Impact factor: 2.454

4. Migratory decarboxylative coupling of coumarins: synthetic and mechanistic aspects.

Authors: Ranjan Jana; James J Partridge; Jon A Tunge
Journal: Angew Chem Int Ed Engl Date: 2011-04-19 Impact factor: 15.336

5. Stereospecific decarboxylative allylation of sulfones.

Authors: Jimmie D Weaver; Being J Ka; David K Morris; Ward Thompson; Jon A Tunge
Journal: J Am Chem Soc Date: 2010-09-08 Impact factor: 15.419

6. Rapid decarboxylative allylation of nitroalkanes.

Authors: Alexander J Grenning; Jon A Tunge
Journal: Org Lett Date: 2010-02-19 Impact factor: 6.005

7. Palladium-catalyzed decarboxylative rearrangements of allyl 2,2,2-trifluoroethyl malonates: direct access to homoallylic esters.

Authors: Lawrence P Tardibono; Jerod Patzner; Cara Cesario; Marvin J Miller
Journal: Org Lett Date: 2009-09-17 Impact factor: 6.005