Literature DB >> 24404374

Carbonium vs. carbenium ion-like transition state geometries for carbocation cyclization - how strain associated with bridging affects 5-exo vs. 6-endo selectivity.

Osvaldo Gutierrez1, Jason G Harrison1, Ryan J Felix2, Fernando Cortés Guzman3, Michel R Gagné2, Dean J Tantillo1.   

Abstract

Quantum chemical calculations are used to explore the origins of regioselectivity for proton-, Pt(II)- and Pd(II)-promoted cyclizations of 1,5-hexadienes, 5-aminoalkenes, and allylic acetimidates. The strain associated with achieving carbonium ion-like transition state geometries is shown to be a key factor in controlling 5-exo vs. 6-endo selectivity.

Entities:  

Year:  2013        PMID： 24404374      PMCID： PMC3882196          DOI： 10.1039/C3SC51657A

Source DB:  PubMed          Journal:  Chem Sci        ISSN： 2041-6520            Impact factor:   9.825


  28 in total

1.  Enzyme Mechanisms for Polycyclic Triterpene Formation.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-08-18       Impact factor: 15.336

2.  A new artificial cyclase for polyprenoids: enantioselective total synthesis of (-)-chromazonarol, (+)-8-epi-puupehedione, and (-)-11'-deoxytaondiol methyl ether.

Authors:  Hideaki Ishibashi; Kazuaki Ishihara; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2004-09-15       Impact factor: 15.419

3.  Synthetic access to bent polycycles by cation-pi cyclization.

Authors:  Ryan A Shenvi; E J Corey
Journal:  Org Lett       Date:  2010-08-06       Impact factor: 6.005

4.  Mechanism of cycloisomerisation of 1,6-heptadienes catalysed by [(tBuCN)2PdCl2]: remarkable influence of exogenous and endogenous 1,6- and 1,5-diene ligands.

Authors:  Katharine L Bray; Guy C Lloyd-Jones; M Paz Muñoz; Paul A Slatford; Emily H P Tan; Amanda R Tyler-Mahon; Paul A Worthington
Journal:  Chemistry       Date:  2006-11-24       Impact factor: 5.236

5.  Palladium-catalyzed alkoxyamination of alkenes with use of N-fluorobenzenesulfonimide as oxidant.

Authors:  Dmitry V Liskin; Paul A Sibbald; Carolyn F Rosewall; Forrest E Michael
Journal:  J Org Chem       Date:  2010-09-17       Impact factor: 4.354

6.  Kinetic and computational analysis of the palladium(II)-catalyzed asymmetric allylic trichloroacetimidate rearrangement: development of a model for enantioselectivity.

Authors:  Mary P Watson; Larry E Overman; Robert G Bergman
Journal:  J Am Chem Soc       Date:  2007-04-03       Impact factor: 15.419

7.  Highly enantioselective proton-initiated polycyclization of polyenes.

Authors:  Karavadhi Surendra; E J Corey
Journal:  J Am Chem Soc       Date:  2012-07-10       Impact factor: 15.419

8.  Enantioselective halocyclization of polyprenoids induced by nucleophilic phosphoramidites.

Authors:  Akira Sakakura; Atsushi Ukai; Kazuaki Ishihara
Journal:  Nature       Date:  2007-02-22       Impact factor: 49.962

9.  Palladium-catalyzed intramolecular hydroalkylation of unactivated olefins with dialkyl ketones.

Authors:  Xiang Wang; Tao Pei; Xiaoqing Han; Ross A Widenhoefer
Journal:  Org Lett       Date:  2003-07-24       Impact factor: 6.005

10.  Mechanistic studies of Wacker-type amidocyclization of alkenes catalyzed by (IMes)Pd(TFA)2(H2O): kinetic and stereochemical implications of proton transfer.

Authors:  Xuan Ye; Paul B White; Shannon S Stahl
Journal:  J Org Chem       Date:  2012-11-30       Impact factor: 4.354
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  1 in total

1.  Electrophilic Pt(II) complexes: precision instruments for the initiation of transformations mediated by the cation-olefin reaction.

Authors:  Ryan J Felix; Colleen Munro-Leighton; Michel R Gagné
Journal:  Acc Chem Res       Date:  2014-05-20       Impact factor: 22.384
  1 in total

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