Literature DB >> 22103775

Ethylene in organic synthesis: a new route to anticholenergic pyrrolidinoindolines, and other molecules with all carbon-quaternary centers via asymmetric hydrovinylation.

Hwan Jung Lim1, T V RajanBabu.   

Abstract

The asymmetric hydrovinylation (1 mol % Ni-cat., 1 atm, ethylene, >98% ee) products from 1-methylenetetralines are readily converted into 3,3-disubstituted oxindoles and subsequently to pyrrolidinoindolines. These hydrovinylation products are also useful for the syntheses of enantiopure benzomorphans.

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Year:  2011        PMID： 22103775      PMCID： PMC3237796          DOI： 10.1021/ol203052y

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


  50 in total

1.  Application of vicarious nucleophilic substitution to the total synthesis of dl-physostigmine.

Authors:  Pankaj D Rege; Francis Johnson
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Review 2.  The taiwaniaquinoids: a review.

Authors:  George Majetich; Joel M Shimkus
Journal:  J Nat Prod       Date:  2010-02-26       Impact factor: 4.050

3.  (R)-3-METHYL-3-PHENYL-1-PENTENE VIA CATALYTIC ASYMMETRIC HYDROVINYLATION.

Authors:  Craig R Smith; Aibin Zhang; Daniel J Mans; T V Rajanbabu; Scott E Denmark; Min Xie
Journal:  Organic Synth       Date:  2008

4.  Organocatalytic asymmetric direct alpha-alkynylation of cyclic beta-ketoesters.

Authors:  Thomas B Poulsen; Luca Bernardi; José Aleman; Jacob Overgaard; Karl Anker Jørgensen
Journal:  J Am Chem Soc       Date:  2007-01-17       Impact factor: 15.419

5.  Asymmetric synthesis of pyrrolidinoindolines. Application for the practical total synthesis of (-)-phenserine.

Authors:  Audris Huang; Jeremy J Kodanko; Larry E Overman
Journal:  J Am Chem Soc       Date:  2004-11-03       Impact factor: 15.419

6.  An efficient synthesis of optically active physostigmine from tryptophan via alkylative cyclization.

Authors:  M Kawahara; A Nishida; M Nakagawa
Journal:  Org Lett       Date:  2000-03-09       Impact factor: 6.005

Review 7.  Azide rearrangements in electron-deficient systems.

Authors:  S Lang; J A Murphy
Journal:  Chem Soc Rev       Date:  2005-11-23       Impact factor: 54.564

8.  Cyclopropylazetoindolines as precursors to C(3)-quaternary-substituted indolines.

Authors:  Vinson R Espejo; Xi-Bo Li; Jon D Rainier
Journal:  J Am Chem Soc       Date:  2010-06-23       Impact factor: 15.419

9.  In Pursuit of an Ideal C-C Bond-Forming Reaction: Development and Applications of the Hydrovinylation of Olefins.

Authors:  T V Rajanbabu
Journal:  Synlett       Date:  2009       Impact factor: 2.454

10.  Palladium-catalyzed enantioselective alpha-arylation and alpha-vinylation of oxindoles facilitated by an axially chiral P-stereogenic ligand.

Authors:  Alexander M Taylor; Ryan A Altman; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-07-29       Impact factor: 15.419
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  4 in total

1.  Asymmetric hydrovinylation of vinylindoles. A facile route to cyclopenta[g]indole natural products (+)-cis-trikentrin A and (+)-cis-trikentrin B.

Authors:  Wang Liu; Hwan Jung Lim; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2012-03-13       Impact factor: 15.419

2.  Recent developments in the catalytic, asymmetric construction of pyrroloindolines bearing all-carbon quaternary stereocenters.

Authors:  Lindsay M Repka; Sarah E Reisman
Journal:  J Org Chem       Date:  2013-12-02       Impact factor: 4.354

Review 3.  Transition-metal-catalyzed laboratory-scale carbon-carbon bond-forming reactions of ethylene.

Authors:  Vaneet Saini; Benjamin J Stokes; Matthew S Sigman
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-17       Impact factor: 15.336

4.  Carbamoyl radical-mediated synthesis and semipinacol rearrangement of β-lactam diols.

Authors:  Marie Betou; Louise Male; Jonathan W Steed; Richard S Grainger
Journal:  Chemistry       Date:  2014-04-07       Impact factor: 5.236
  4 in total

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