Literature DB >> 21504208

Regioselective hydroformylation of allylic alcohols.

Thomas E Lightburn1, Omar A De Paolis, Ka H Cheng, Kian L Tan.   

Abstract

A highly regioselective hydroformylation of allylic alcohols is reported toward the synthesis of β-hydroxy-acid and aldehyde products. The selectivity is achieved through the use of a ligand that reversibly binds to alcohols in situ, allowing for a directed hydroformylation to occur. The application to trisubstituted olefins was also demonstrated, which yields a single diastereomer product consistent with a stereospecific addition of CO and hydrogen.

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Year:  2011        PMID: 21504208      PMCID: PMC3096926          DOI: 10.1021/ol200782d

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


  31 in total

1.  Synthetic aspects of stereoselective hydroformylation.

Authors:  Bernhard Breit
Journal:  Acc Chem Res       Date:  2003-04       Impact factor: 22.384

2.  High-yielding tandem hydroformylation/hydrogenation of a terminal olefin to produce a linear alcohol using a Rh/Ru dual catalyst system.

Authors:  Kohei Takahashi; Makoto Yamashita; Takeo Ichihara; Koji Nakano; Kyoko Nozaki
Journal:  Angew Chem Int Ed Engl       Date:  2010-06-14       Impact factor: 15.336

3.  Reagent directing group controlled organic synthesis: total synthesis of (R,R,R)-alpha-tocopherol.

Authors:  Christian Rein; Peter Demel; Robert A Outten; Thomas Netscher; Bernhard Breit
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  The catalytic intermolecular orthoarylation of phenols.

Authors:  Robin B Bedford; Simon J Coles; Michael B Hursthouse; Michael E Limmert
Journal:  Angew Chem Int Ed Engl       Date:  2003-01-03       Impact factor: 15.336

5.  Total synthesis of (+)-clavolonine, (-)-deacetylfawcettiine, and (+)-acetylfawcettiine.

Authors:  Kai M Laemmerhold; Bernhard Breit
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-22       Impact factor: 15.336

6.  Remote control of regio- and diastereoselectivity in the hydroformylation of bishomoallylic alcohols with catalytic amounts of a reversibly bound directing group.

Authors:  Christian U Grünanger; Bernhard Breit
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

7.  Phosphabenzenes as monodentate pi-acceptor ligands for rhodium-catalyzed hydroformylation.

Authors:  B Breit; R Winde; T Mackewitz; R Paciello; K Harms
Journal:  Chemistry       Date:  2001-07-16       Impact factor: 5.236

8.  Application of a chiral scaffolding ligand in catalytic enantioselective hydroformylation.

Authors:  Amanda D Worthy; Candice L Joe; Thomas E Lightburn; Kian L Tan
Journal:  J Am Chem Soc       Date:  2010-10-27       Impact factor: 15.419

9.  Enantioselective hydroformylation of N-vinyl carboxamides, allyl carbamates, and allyl ethers using chiral diazaphospholane ligands.

Authors:  Richard I McDonald; Gene W Wong; Ram P Neupane; Shannon S Stahl; Clark R Landis
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

10.  Enantioselective synthesis of 2,6-dideoxy carbasugars based on a desymmetrizing hydroformylation-carbonyl ene cyclization process.

Authors:  Bernhard Breit; Aurélien Bigot
Journal:  Chem Commun (Camb)       Date:  2008-11-11       Impact factor: 6.222

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  5 in total

1.  Scaffolding catalysts: highly enantioselective desymmetrization reactions.

Authors:  Xixi Sun; Amanda D Worthy; Kian L Tan
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-07       Impact factor: 15.336

2.  Scaffolding Catalysis: Expanding the Repertoire of Bifunctional Catalysts.

Authors:  Kian L Tan; Xixi Sun; Amanda D Worthy
Journal:  Synlett       Date:  2012-02-01       Impact factor: 2.454

3.  Enantioselective hydroformylation of aniline derivatives.

Authors:  Candice L Joe; Kian L Tan
Journal:  J Org Chem       Date:  2011-08-15       Impact factor: 4.354

4.  Highly stereoselective C-C bond formation by rhodium-catalyzed tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor carbenoids and chiral allylic alcohols.

Authors:  Zhanjie Li; Brendan T Parr; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2012-06-25       Impact factor: 15.419

5.  Distal-selective hydroformylation using scaffolding catalysis.

Authors:  Candice L Joe; Thomas P Blaisdell; Allison F Geoghan; Kian L Tan
Journal:  J Am Chem Soc       Date:  2014-06-06       Impact factor: 15.419

  5 in total

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