Literature DB >> 33824546

Preparation of Enantioenriched Alkylcarbastannatranes via Nucleophilic Inversion of Alkyl Mesylates for Use in Stereospecific Cross-Coupling Reactions.

Glenn Ralph1,2, Mark R Biscoe1,2.   

Abstract

We report the preparation of enantioenriched secondary alkylcarbastannatranes via a stereoinvertive SN2 reaction of enantioenriched alkyl mesylates and carbastannatranyl anion equivalents. Using this process, enantioenriched secondary alcohols may be converted into highly enantioenriched alkylcarbastannatranes, which are useful in stereospecific cross-coupling reactions.

Entities:  

Year:  2019        PMID： 33824546      PMCID： PMC8021098          DOI： 10.1021/acs.organomet.9b00467

Source DB:  PubMed          Journal:  Organometallics        ISSN： 0276-7333            Impact factor:   3.876


  18 in total

1.  Changes in Tricarbastannatrane Transannular N-Sn Bonding upon Complexation Reveal Lewis Base Donicities.

Authors:  Petar Simidzija; Michael J Lecours; Rick A Marta; Vincent Steinmetz; Terrance B McMahon; Eric Fillion; W Scott Hopkins
Journal:  Inorg Chem       Date:  2016-09-15       Impact factor: 5.165

2.  Enantiodivergent Pd-catalyzed C-C bond formation enabled through ligand parameterization.

Authors:  Shibin Zhao; Tobias Gensch; Benjamin Murray; Zachary L Niemeyer; Matthew S Sigman; Mark R Biscoe
Journal:  Science       Date:  2018-09-20       Impact factor: 47.728

3.  B(C6F5)3-Catalyzed transfer 1,4-hydrostannylation of α,β-unsaturated carbonyls using iPr-tricarbastannatrane.

Authors:  Eric Fillion; Azadeh Kavoosi; Kevin Nguyen; Christian Ieritano
Journal:  Chem Commun (Camb)       Date:  2016-10-25       Impact factor: 6.222

4.  Stereospecific Electrophilic Fluorination of Alkylcarbastannatrane Reagents.

Authors:  Xinghua Ma; Mohamed Diane; Glenn Ralph; Christine Chen; Mark R Biscoe
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-04       Impact factor: 15.336

5.  Alkyl Carbagermatranes Enable Practical Palladium-Catalyzed sp2-sp3 Cross-Coupling.

Authors:  Meng-Yu Xu; Wei-Tao Jiang; Ying Li; Qing-Hao Xu; Qiao-Lan Zhou; Shuo Yang; Bin Xiao
Journal:  J Am Chem Soc       Date:  2019-04-25       Impact factor: 15.419

6.  Stille coupling of an aziridinyl stannatrane.

Authors:  Naresh Theddu; Edwin Vedejs
Journal:  J Org Chem       Date:  2013-04-25       Impact factor: 4.354

7.  Cine-substitution in the Stille coupling: evidence for the carbenoid reactivity of sp3-gem-organodimetallic iodopalladio-trialkylstannylalkane intermediates.

Authors:  Eric Fillion; Nicholas J Taylor
Journal:  J Am Chem Soc       Date:  2003-10-22       Impact factor: 15.419

8.  Synthesis and characterization of tricarbastannatranes and their reactivity in B(C6F5)3-promoted conjugate additions.

Authors:  Azadeh Kavoosi; Eric Fillion
Journal:  Angew Chem Int Ed Engl       Date:  2015-03-05       Impact factor: 15.336

9.  Stereoretentive Pd-catalysed Stille cross-coupling reactions of secondary alkyl azastannatranes and aryl halides.

Authors:  Ling Li; Chao-Yuan Wang; Rongcai Huang; Mark R Biscoe
Journal:  Nat Chem       Date:  2013-05-19       Impact factor: 24.427

10.  Configurationally Stable, Enantioenriched Organometallic Nucleophiles in Stereospecific Pd-Catalyzed Cross-Coupling Reactions: An Alternative Approach to Asymmetric Synthesis.

Authors:  Chao-Yuan Wang; Joseph Derosaa; Mark R Biscoe
Journal:  Chem Sci       Date:  2015       Impact factor: 9.825
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.