Literature DB >> 26091063

Enantioselective Hydroformylation of 1-Alkenes with Commercial Ph-BPE Ligand.

Zhiyong Yu1, Meredith S Eno1, Alexandra H Annis1, James P Morken1.   

Abstract

A rhodium complex, in conjunction with commercially available Ph-BPE ligand, catalyzes the branch-selective asymmetric hydroformylation of 1-alkenes and rapidly generates α-chiral aldehydes. A wide range of terminal olefins including 1-dodecene were examined, and all delivered high enantioselectivity (up to 98:2 er) as well as good branch:linear ratios (up to 15:1).

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Year:  2015        PMID： 26091063      PMCID： PMC4608024          DOI： 10.1021/acs.orglett.5b01421

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


  16 in total

1.  Regio- and diastereoselective tandem rhodium-catalyzed allylic alkylation/Pauson-Khand annulation reactions.

Authors:  P A Evans; J E Robinson
Journal:  J Am Chem Soc       Date:  2001-05-16       Impact factor: 15.419

2.  Total synthesis and structural elucidation of khafrefungin.

Authors:  T Wakabayashi; K Mori; S Kobayashi
Journal:  J Am Chem Soc       Date:  2001-02-21       Impact factor: 15.419

3.  Asymmetric hydroformylation-initiated tandem sequences for syntheses of (+)-patulolide C, (-)-pyrenophorol, (+)-decarestrictine L, and (+)-prelog djerassi lactone.

Authors:  Roberto M Risi; Andrew M Maza; Steven D Burke
Journal:  J Org Chem       Date:  2014-12-01       Impact factor: 4.354

4.  New chiral phosphorus ligands for enantioselective hydrogenation.

Authors:  Wenjun Tang; Xumu Zhang
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

5.  An asymmetric hydroformylation catalyst that delivers branched aldehydes from alkyl alkenes.

Authors:  Gary M Noonan; José A Fuentes; Christopher J Cobley; Matthew L Clarke
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-27       Impact factor: 15.336

6.  Highly regio- and enantioselective asymmetric hydroformylation of olefins mediated by 2,5-disubstituted phospholane ligands.

Authors:  Alex T Axtell; Christopher J Cobley; Jerzy Klosin; Gregory T Whiteker; Antonio Zanotti-Gerosa; Khalil A Abboud
Journal:  Angew Chem Int Ed Engl       Date:  2005-09-12       Impact factor: 15.336

7.  Regioselective rhodium-catalyzed hydroformylation of 1,3-dienes to highly enantioenriched β,γ-unsaturated aldehyes with diazaphospholane ligands.

Authors:  Avery L Watkins; Clark R Landis
Journal:  Org Lett       Date:  2010-12-06       Impact factor: 6.005

8.  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

9.  Solvent-free asymmetric olefin hydroformylation catalyzed by highly cross-linked polystyrene-supported (R,S)-BINAPHOS-Rh(I) complex.

Authors:  Fumitoshi Shibahara; Kyoko Nozaki; Tamejiro Hiyama
Journal:  J Am Chem Soc       Date:  2003-07-16       Impact factor: 15.419

10.  Enantioselective redox-relay oxidative heck arylations of acyclic alkenyl alcohols using boronic acids.

Authors:  Tian-Sheng Mei; Erik W Werner; Alexander J Burckle; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2013-04-24       Impact factor: 15.419
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  2 in total

1.  Evolution of an Efficient and Scalable Nine-Step (Longest Linear Sequence) Synthesis of Zincophorin Methyl Ester.

Authors:  Liang-An Chen; Melissa A Ashley; James L Leighton
Journal:  J Am Chem Soc       Date:  2017-03-15       Impact factor: 15.419

2.  Enantioselective Synthesis of 4-Methyl-3,4-dihydroisocoumarin via Asymmetric Hydroformylation of Styrene Derivatives.

Authors:  Bo Qu; Renchang Tan; Madison R Herling; Nizar Haddad; Nelu Grinberg; Marisa C Kozlowski; Xumu Zhang; Chris H Senanayake
Journal:  J Org Chem       Date:  2019-03-06       Impact factor: 4.354
  2 in total

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