Literature DB >> 17760452

Asymmetric intermolecular heck-type reaction of acyclic alkenes via oxidative palladium(II) catalysis.

Kyung Soo Yoo1, Chan Pil Park, Cheol Hwan Yoon, Satoshi Sakaguchi, Justin O'Neill, Kyung Woon Jung.   

Abstract

Herein, we report an asymmetric intermolecular Heck-type reaction of acyclic alkenes by using a palladium-pyridinyl oxazoline diacetate complex under oxidative palladium(II) catalysis conditions. A premade palladium-ligand complex afforded higher enantioselectivities than a corresponding premixed palladium-ligand system, while offering enhanced asymmetric induction when compared to known intermolecular Heck-type protocols.

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Year:  2007        PMID： 17760452     DOI： 10.1021/ol701584f

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


  24 in total

1.  Allylic C-H acetoxylation with a 4,5-diazafluorenone-ligated palladium catalyst: a ligand-based strategy to achieve aerobic catalytic turnover.

Authors:  Alison N Campbell; Paul B White; Ilia A Guzei; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2010-11-03       Impact factor: 15.419

2.  Mechanism and enantioselectivity in palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones: insights from computation and experiment.

Authors:  Jeffrey C Holder; Lufeng Zou; Alexander N Marziale; Peng Liu; Yu Lan; Michele Gatti; Kotaro Kikushima; K N Houk; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2013-09-27       Impact factor: 15.419

3.  Aerobic alcohol oxidation coupled to palladium-catalyzed alkene hydroarylation with boronic esters.

Authors:  Yasumasa Iwai; Keith M Gligorich; Matthew S Sigman
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Relative reactivity of alkenyl alcohols in the palladium-catalyzed redox-relay Heck reaction.

Authors:  Margaret J Hilton; Bin Cheng; Benjamin R Buckley; Liping Xu; Olaf Wiest; Matthew S Sigman
Journal:  Tetrahedron       Date:  2015-09-16       Impact factor: 2.457

5.  Enantioselective Heck arylations of acyclic alkenyl alcohols using a redox-relay strategy.

Authors:  Erik W Werner; Tian-Sheng Mei; Alexander J Burckle; Matthew S Sigman
Journal:  Science       Date:  2012-12-14       Impact factor: 47.728

6.  Preparation of (S)-tert-ButylPyOx and Palladium-catalyzed Asymmetric Conjugate Addition of Arylboronic Acids.

Authors:  Jeffrey C Holder; Samantha E Shockley; Mario P Wiesenfeldt; Hideki Shimizu; Brian M Stoltz
Journal:  Organic Synth       Date:  2016-03-04

7.  Asymmetric intermolecular boron Heck-type reactions via oxidative palladium(II) catalysis with chiral tridentate NHC-amidate-alkoxide ligands.

Authors:  Kyung Soo Yoo; Justin O'Neill; Satoshi Sakaguchi; Richard Giles; Joo Ho Lee; Kyung Woon Jung
Journal:  J Org Chem       Date:  2010-01-01       Impact factor: 4.354

8.  Aerobic oxidative Heck/dehydrogenation reactions of cyclohexenones: efficient access to meta-substituted phenols.

Authors:  Yusuke Izawa; Changwu Zheng; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-19       Impact factor: 15.336

9.  Reconciling the stereochemical course of nucleopalladation with the development of enantioselective wacker-type cyclizations.

Authors:  Adam B Weinstein; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-16       Impact factor: 15.336

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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