Literature DB >> 29676895

Stereodivergent Catalysis.

Irina P Beletskaya1, Carmen Nájera2, Miguel Yus2.   

Abstract

This review covers diastereo- and enantiodivergent catalyzed reactions in acyclic and cyclic systems using metal complexes or organocatalysts. Among them, nucleophilic addition to carbon-carbon and carbon-nitrogen double bonds, α-functionalization of carbonyl compounds, allylic substitutions, and ring opening of oxiranes and aziridines are considered. The diastereodivergent synthesis of alkenes from alkynes is also included. Finally, stereodivergent intramolecular and intermolecular cycloadditions and other cyclizations are also reported.

Entities:  

Year:  2018        PMID: 29676895     DOI: 10.1021/acs.chemrev.7b00561

Source DB:  PubMed          Journal:  Chem Rev        ISSN: 0009-2665            Impact factor:   60.622


  25 in total

Review 1.  Engaging Aldehydes in CuH-Catalyzed Reductive Coupling Reactions: Stereoselective Allylation with Unactivated 1,3-Diene Pronucleophiles.

Authors:  Chengxi Li; Kwangmin Shin; Richard Y Liu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-22       Impact factor: 15.336

2.  Inversion of Enantioselectivity in Allene Gas versus Allyl Acetate Reductive Aldehyde Allylation Guided by Metal-Centered Stereogenicity: An Experimental and Computational Study.

Authors:  Seung Wook Kim; Cole C Meyer; Binh Khanh Mai; Peng Liu; Michael J Krische
Journal:  ACS Catal       Date:  2019-09-11       Impact factor: 13.084

3.  Diastereodivergent Synthesis of Hexahydro-6H-benzo[c]chromen-6-one Derivatives Catalyzed by Modularly Designed Organocatalysts.

Authors:  Satish Jakkampudi; Ramarao Parella; Hadi D Arman; John C-G Zhao
Journal:  Chemistry       Date:  2019-05-09       Impact factor: 5.236

4.  Stereodivergent, Chemoenzymatic Synthesis of Azaphilone Natural Products.

Authors:  Joshua B Pyser; Summer A Baker Dockrey; Attabey Rodríguez Benítez; Leo A Joyce; Ren A Wiscons; Janet L Smith; Alison R H Narayan
Journal:  J Am Chem Soc       Date:  2019-11-06       Impact factor: 15.419

5.  DFT-Based Stereochemical Rationales for the Bifunctional Brønsted Acid/Base-Catalyzed Diastereodivergent and Enantioselective aza-Henry Reactions of α-Nitro Esters.

Authors:  Thomas J Struble; Ivor Smajlagic; Hayden Foy; Travis Dudding; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2021-10-20       Impact factor: 4.354

6.  Catalytic Enantioselective Hydrovinylation of Trialkylsilyloxy and Acetoxy-1,3-Dienes: Cationic Co(I) Complexes for the Synthesis of Chiral Enolate Surrogates and Their Applications for Synthesis of Ketones and Cross-Coupling Reagents in High Enantiomeric Purity.

Authors:  Souvagya Biswas; Kendra R Dewese; Balaram Raya; T V RajanBabu
Journal:  ACS Catal       Date:  2022-04-14       Impact factor: 13.700

7.  Ligand-dependent, palladium-catalyzed stereodivergent synthesis of chiral tetrahydroquinolines.

Authors:  Yue Wang; Er-Qing Li; Zheng Duan
Journal:  Chem Sci       Date:  2022-06-20       Impact factor: 9.969

8.  Confronting the Challenging Asymmetric Carbonyl 1,2-Addition Using Vinyl Heteroarene Pronucleophiles: Ligand-Controlled Regiodivergent Processes through a Dearomatized Allyl-Cu Species.

Authors:  Yuyang Dong; Alexander W Schuppe; Binh Khanh Mai; Peng Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2022-03-26       Impact factor: 16.383

9.  A Diastereodivergent and Enantioselective Approach to syn- and anti-Diamines: Development of 2-Azatrienes for Cu-Catalyzed Reductive Couplings with Imines That Furnish Allylic Amines.

Authors:  Pengfei Zhou; Xinxin Shao; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2021-08-23       Impact factor: 16.383

10.  Stereodivergent Nucleophilic Additions to Racemic β-Oxo Acid Derivatives: Fast Addition Outcompetes Stereoconvergence in the Archetypal Configurationally Unstable Electrophile.

Authors:  Pedro De Jesús Cruz; Evan T Crawford; Shubin Liu; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2021-09-27       Impact factor: 16.383

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