Literature DB >> 16468806

Palladium(0)-catalyzed synthesis of chiral ene-allenes using alkenyl trifluoroborates.

Gary A Molander1, Erin M Sommers, Sharon R Baker.   

Abstract

Enantioenriched allenes serve as chiral transfer reagents, making them attractive synthetic targets. Herein, the synthesis of enantioenriched allenes utilizing a Pd(0)-catalyzed cross-coupling reaction of propargylic carbonates and phosphates with alkenyl trifluoroborates is reported. Di-, tri-, and tetrasubstituted allenes were synthesized in moderate to high optical yields. Several racemic allenes possessing various functional groups were also synthesized.

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Year:  2006        PMID： 16468806      PMCID： PMC2504514          DOI： 10.1021/jo052201x

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  18 in total

1.  Key process in palladium-catalyzed asymmetric transformation of propargyl electrophiles. Racemization of optically active eta1-allenylpalladium(II).

Authors:  S Ogoshi; T Nishida; T Shinagawa; H Kurosawa
Journal:  J Am Chem Soc       Date:  2001-07-25       Impact factor: 15.419

2.  Enantioselective addition of 2-methyl-3-butyn-2-ol to aldehydes: preparation of 3-hydroxy-1-butynes

Authors: 
Journal:  Org Lett       Date:  2000-12-28       Impact factor: 6.005

3.  Asymmetric synthesis of gamma-hydroxy alpha,beta-unsaturated aldehydes via enantioselective direct addition of propargyl acetate to aldehydes.

Authors:  E El-Sayed; N K Anand; E M Carreira
Journal:  Org Lett       Date:  2001-09-20       Impact factor: 6.005

4.  Chloroprene as a source of fine chemicals: palladium-catalyzed synthesis of terminal allenes.

Authors:  M Ogasawara; H Ikeda; T Nagano; T Hayashi
Journal:  Org Lett       Date:  2001-08-09       Impact factor: 6.005

Review 5.  The discovery of novel reactivity in the development of C-C bond-forming reactions: in situ generation of zinc acetylides with Zn(II)/R(3)N.

Authors:  D E Frantz; R Fassler; C S Tomooka; E M Carreira
Journal:  Acc Chem Res       Date:  2000-06       Impact factor: 22.384

6.  Synthesis of enantiomerically enriched allenes by (-)-sparteine-mediated lithiation of alkynyl carbamates.

Authors:  C Schultz-Fademrecht; B Wibbeling; R Fröhlich; D Hoppe
Journal:  Org Lett       Date:  2001-04-19       Impact factor: 6.005

7.  Systematic synthesis of Bis-THF ring cores in annonaceous acetogenins.

Authors:  Naoyoshi Maezaki; Naoto Kojima; Hiroaki Tominaga; Minori Yanai; Tetsuaki Tanaka
Journal:  Org Lett       Date:  2003-05-01       Impact factor: 6.005

8.  Highly enantioselective alkynylation of alpha-keto ester: an efficient method for constructing a chiral tertiary carbon center.

Authors:  Biao Jiang; Zili Chen; Xiaoxia Tang
Journal:  Org Lett       Date:  2002-10-03       Impact factor: 6.005

Review 9.  Synthesis and properties of allenic natural products and pharmaceuticals.

Authors:  Anja Hoffmann-Röder; Norbert Krause
Journal:  Angew Chem Int Ed Engl       Date:  2004-02-27       Impact factor: 15.336

10.  gem-Silylborylation of an sp carbon: novel synthesis of 1-boryl-1-silylallenes.

Authors:  Masaki Shimizu; Takuya Kurahashi; Hirotaka Kitagawa; Tamejiro Hiyama
Journal:  Org Lett       Date:  2003-01-23       Impact factor: 6.005
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  10 in total

1.  Construction of 1,5-enynes by stereospecific Pd-catalyzed allyl-propargyl cross-couplings.

Authors:  Michael J Ardolino; James P Morken
Journal:  J Am Chem Soc       Date:  2012-05-17       Impact factor: 15.419

2.  Synthesis of functionalized organotrifluoroborates via the 1,3-dipolar cycloaddition of azides.

Authors:  Gary A Molander; Jungyeob Ham
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

3.  Linchpin synthons: metalation of aryl bromides bearing a potassium trifluoroborate moiety.

Authors:  Gary A Molander; Noel M Ellis
Journal:  J Org Chem       Date:  2006-09-15       Impact factor: 4.354

4.  Chiral allene-containing phosphines in asymmetric catalysis.

Authors:  Feng Cai; Xiaotao Pu; Xiangbing Qi; Vincent Lynch; Akella Radha; Joseph M Ready
Journal:  J Am Chem Soc       Date:  2011-10-21       Impact factor: 15.419

5.  Combining NHC-Cu and Brønsted base catalysis: enantioselective allylic substitution/conjugate additions with alkynylaluminum reagents and stereospecific isomerization of the products to trisubstituted allenes.

Authors:  Jennifer A Dabrowski; Fredrik Haeffner; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-18       Impact factor: 15.336

6.  Facile Synthesis of Clickable, Water-soluble and Degradable Polyphosphoesters.

Authors:  Shiyi Zhang; Ang Li; Jiong Zou; Lily Yun Lin; Karen L Wooley
Journal:  ACS Macro Lett       Date:  2012-02-03       Impact factor: 6.903

7.  Palladium-catalyzed cross-coupling reaction of alkenyl bromides with potassium alkyltrifluoroborates.

Authors:  Gary A Molander; Jungyeob Ham; Dave G Seapy
Journal:  Tetrahedron       Date:  2007-01-15       Impact factor: 2.457

8.  Enantioselective Synthesis of Trisubstituted Allenyl-B(pin) Compounds by Phosphine-Cu-Catalyzed 1,3-Enyne Hydroboration. Insights Regarding Stereochemical Integrity of Cu-Allenyl Intermediates.

Authors:  Youming Huang; Juan Del Pozo; Sebastian Torker; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2018-02-08       Impact factor: 15.419

9.  Palladium-catalyzed chemoselective allylic substitution, Suzuki-Miyaura cross-coupling, and allene formation of bifunctional 2-B(pin)-substituted allylic acetate derivatives.

Authors:  Byeong-Seon Kim; Mahmud M Hussain; Nusrah Hussain; Patrick J Walsh
Journal:  Chemistry       Date:  2014-07-30       Impact factor: 5.236

10.  Stereocontrol in Palladium-Catalyzed Propargylic Substitutions: Kinetic Resolution to give Enantioenriched 1,5-Enynes and Propargyl Acetates.

Authors:  Michael J Ardolino; Meredith S Eno; James P Morken
Journal:  Adv Synth Catal       Date:  2013-11-25       Impact factor: 5.837
  10 in total

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