Literature DB >> 16492045

Synthetic studies and mechanistic insight in nickel-catalyzed [4+2+1] cycloadditions.

Yike Ni1, John Montgomery.   

Abstract

A new nickel-catalyzed procedure for the [4+2+1] cycloaddition of (trimethylsilyl)diazomethane with alkynes tethered to dienes has been developed. A broad range of unsaturated substrates participate in the sequence, and stereoselectivities are generally excellent. Stereochemical studies provided evidence for a mechanism that involves the [3,3] sigmatropic rearrangement of divinylcyclopropanes.

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Year:  2006        PMID： 16492045      PMCID： PMC2720272          DOI： 10.1021/ja057741q

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


  21 in total

1.  The dienyl Pauson-Khand reaction.

Authors:  Paul A Wender; Nicole M Deschamps; Gabriel G Gamber
Journal:  Angew Chem Int Ed Engl       Date:  2003-04-25       Impact factor: 15.336

2.  Efficient protiodesilylation of unactivated C(sp3)-SiMe2Ph bonds using tetrabutylammonium fluoride.

Authors:  Cheryl L Heitzman; William T Lambert; Eric Mertz; J Brad Shotwell; Jennifer M Tinsley; Porino Va; William R Roush
Journal:  Org Lett       Date:  2005-06-09       Impact factor: 6.005

3.  Metal carbene-promoted sequential transformations for the enantioselective synthesis of highly functionalized cycloheptadienes.

Authors:  Liang Deng; Anthony J Giessert; Oksana O Gerlitz; Xing Dai; Steven T Diver; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2005-02-09       Impact factor: 15.419

4.  An exploratory study of type II [3 + 4] cycloadditions between vinylcarbenoids and dienes.

Authors:  H M Davies; R L Calvo; R J Townsend; P Ren; R M Churchill
Journal:  J Org Chem       Date:  2000-07-14       Impact factor: 4.354

5.  Multicomponent cycloadditions: the four-component [5+1+2+1] cycloaddition of vinylcyclopropanes, alkynes, and CO.

Authors:  Paul A Wender; Gabriel G Gamber; Robert D Hubbard; Son M Pham; Lei Zhang
Journal:  J Am Chem Soc       Date:  2005-03-09       Impact factor: 15.419

6.  Tandem cyclopropanation/ring-closing metathesis of dienynes.

Authors:  Brian P Peppers; Steven T Diver
Journal:  J Am Chem Soc       Date:  2004-08-11       Impact factor: 15.419

7.  Rhodium catalyzed [4 + 2 + 2] cycloaddition and alkyne insertion: a new route to eight-membered rings.

Authors:  Scott R Gilbertson; Brenton DeBoef
Journal:  J Am Chem Soc       Date:  2002-07-31       Impact factor: 15.419

8.  N-heterocyclic carbenes: a new concept in organometallic catalysis.

Authors:  Wolfgang A Herrmann
Journal:  Angew Chem Int Ed Engl       Date:  2002-04-15       Impact factor: 15.336

9.  Synthesis, structure, and reactions of a three-coordinate nickel-carbene complex, [1,2-Bis(di-tert-butylphosphino)ethane]Ni=CPh(2).

Authors:  Daniel J Mindiola; Gregory L Hillhouse
Journal:  J Am Chem Soc       Date:  2002-08-28       Impact factor: 15.419

10.  Ligand-dependent scope and divergent mechanistic behavior in nickel-catalyzed reductive couplings of aldehydes and alkynes.

Authors:  Gireesh M Mahandru; Gang Liu; John Montgomery
Journal:  J Am Chem Soc       Date:  2004-03-31       Impact factor: 15.419
View more
  5 in total

1.  Nickel-Catalyzed Reductive [2+2] Cycloaddition of Alkynes.

Authors:  Santiago Cañellas; John Montgomery; Miquel À Pericàs
Journal:  J Am Chem Soc       Date:  2018-12-10       Impact factor: 15.419

2.  Rhodium(III)-catalyzed oxidative carbonylation of benzamides with carbon monoxide.

Authors:  Ya Du; Todd K Hyster; Tomislav Rovis
Journal:  Chem Commun (Camb)       Date:  2011-10-17       Impact factor: 6.222

Review 3.  Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.

Authors:  Amanda C Jones; Jeremy A May; Richmond Sarpong; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-03       Impact factor: 15.336

Review 4.  Recent Advances in Catalytic Alkyne Transformation via Copper Carbene Intermediates.

Authors:  Kuiyong Dong; Mengting Liu; Xinfang Xu
Journal:  Molecules       Date:  2022-05-11       Impact factor: 4.927

5.  Controlling Enantioselectivity and Diastereoselectivity in Radical Cascade Cyclization for Construction of Bicyclic Structures.

Authors:  Congzhe Zhang; Duo-Sheng Wang; Wan-Chen Cindy Lee; Alexander M McKillop; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2021-07-14       Impact factor: 16.383
  5 in total

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