Literature DB >> 24353484

The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups.

Barry M Trost1, Andrew H Weiss2.   

Abstract

Over the past decade, large strides have been achieved in the invention of methods for the direct enantioselective addition of alkynes and metal alkynylide nucleophiles into prochiral aldehydes, ketones, and imines. This review highlights and compares the available methods for these transformations.

Entities:  

Keywords:  alkynylation; catalytic asymmetric; propargylic alcohol; propargylic amine

Year:  2009        PMID： 24353484      PMCID： PMC3864370          DOI： 10.1002/adsc.200800776

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN： 1615-4150            Impact factor:   5.837


  71 in total

1.  A mild method for the preparation of gamma-hydroxy-alpha,beta-acetylenic esters.

Authors:  Shatrughan P Shahi; Kazunori Koide
Journal:  Angew Chem Int Ed Engl       Date:  2004-05-03       Impact factor: 15.336

2.  Total synthesis of FR901464, an antitumor agent that regulates the transcription of oncogenes and tumor suppressor genes.

Authors:  Brian J Albert; Ananthapadmanabhan Sivaramakrishnan; Tadaatsu Naka; Kazunori Koide
Journal:  J Am Chem Soc       Date:  2006-03-08       Impact factor: 15.419

Review 3.  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

4.  Asymmetric synthesis of propargylamides via 3,3'-disubstituted binaphthol-modified alkynylboronates.

Authors:  T Robert Wu; J Michael Chong
Journal:  Org Lett       Date:  2006-01-05       Impact factor: 6.005

5.  BINOL-catalyzed highly enantioselective terminal alkyne additions to aromatic aldehydes.

Authors:  David Moore; Lin Pu
Journal:  Org Lett       Date:  2002-05-30       Impact factor: 6.005

6.  Highly efficient Grignard-type imine additions via C-H activation in water and under solvent-free conditions.

Authors:  Chao-Jun Li; Chunmei Wei
Journal:  Chem Commun (Camb)       Date:  2002-02-07       Impact factor: 6.222

7.  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

8.  Enantioselective alkynylation of aldehydes catalyzed by [2.2]paracyclophane-based ligands.

Authors:  Stefan Dahmen
Journal:  Org Lett       Date:  2004-06-24       Impact factor: 6.005

9.  Infrared spectroscopic investigations on the metallation of terminal alkynes by Zn(OTf)2.

Authors:  Roger Fässler; Craig S Tomooka; Doug E Frantz; Erick M Carreira
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-05       Impact factor: 11.205

10.  Highly enantioselective alkyne additions to aldehydes in the presence of 1,1'-bi-2-naphthol and hexamethylphosphoramide.

Authors:  Ge Gao; Ru-Gang Xie; Lin Pu
Journal:  Proc Natl Acad Sci U S A       Date:  2004-03-16       Impact factor: 11.205
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  30 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.  Direct Conversion of Primary Alcohols to 1,2-Amino Alcohols: Enantioselective Iridium-Catalyzed Carbonyl Reductive Coupling of Phthalimido-Allene via Hydrogen Auto-Transfer.

Authors:  Kim Spielmann; Ming Xiang; Leyah A Schwartz; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-08-29       Impact factor: 15.419

3.  Gold-catalyzed one-step practical synthesis of oxetan-3-ones from readily available propargylic alcohols.

Authors:  Longwu Ye; Weimin He; Liming Zhang
Journal:  J Am Chem Soc       Date:  2010-06-30       Impact factor: 15.419

4.  Total and Formal Syntheses of Fostriecin.

Authors:  Gao Dong; Bohui Li; George O'Doherty
Journal:  Org Chem Front       Date:  2020-10-12       Impact factor: 5.281

5.  Efficient and General Synthesis of 3-Aminoindolines and 3-Aminoindoles via Copper-Catalyzed Three Component Coupling Reaction.

Authors:  Dmitri Chernyak; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Adv Synth Catal       Date:  2010-04-19       Impact factor: 5.837

6.  Rhodium-Catalyzed Aldehyde Arylation via Formate-Mediated Transfer Hydrogenation: Beyond Metallic Reductants in Grignard/Nozaki-Hiyami-Kishi-Type Addition.

Authors:  Robert A Swyka; Wandi Zhang; Jeffery Richardson; J Craig Ruble; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-01-29       Impact factor: 15.419

7.  A new strategy for the synthesis of chiral β-alkynyl esters via sequential palladium and copper catalysis.

Authors:  Barry M Trost; Benjamin R Taft; James T Masters; Jean-Philip Lumb
Journal:  J Am Chem Soc       Date:  2011-05-16       Impact factor: 15.419

8.  Direct Zinc(II)-Catalyzed Enantioconvergent Additions of Terminal Alkynes to α-Keto Esters.

Authors:  Blane P Zavesky; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-20       Impact factor: 15.336

9.  Development of Zn-ProPhenol-catalyzed asymmetric alkyne addition: synthesis of chiral propargylic alcohols.

Authors:  Barry M Trost; Mark J Bartlett; Andrew H Weiss; Axel Jacobi von Wangelin; Vincent S Chan
Journal:  Chemistry       Date:  2012-10-23       Impact factor: 5.236

10.  Direct Conversion of N-Alkylamines to N-Propargylamines through C-H Activation Promoted by Lewis Acid/Organocopper Catalysis: Application to Late-Stage Functionalization of Bioactive Molecules.

Authors:  Jessica Z Chan; Ahmet Yesilcimen; Min Cao; Yuyang Zhang; Bochao Zhang; Masayuki Wasa
Journal:  J Am Chem Soc       Date:  2020-09-11       Impact factor: 15.419
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