Literature DB >> 23959006

Direct asymmetric syntheses of chiral aldehydes and ketones via N-acyl chiral auxiliary derivatives including chiral Weinreb amide equivalents.

Stephen G Davies1, Ai M Fletcher, James E Thomson.   

Abstract

This article covers N-acyl chiral auxiliary-based approaches to the asymmetric synthesis of enantiopure aldehydes and ketones. The use of diastereoisomerically pure N-acyl derivatives of chiral auxiliaries (including chiral Weinreb amide equivalents) and their conversion to the corresponding enantiopure aldehydes and ketones in a single synthetic operation by treatment with a hydride reducing agent or an organometallic reagent, respectively, are highlighted.

Entities:  

Year:  2013        PMID: 23959006     DOI: 10.1039/c3cc45463k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  6 in total

1.  Vinyl Triflate-Aldehyde Reductive Coupling-Redox Isomerization Mediated by Formate: Rhodium-Catalyzed Ketone Synthesis in the Absence of Stoichiometric Metals.

Authors:  William G Shuler; Robert A Swyka; Tabitha T Schempp; Brian J Spinello; Michael J Krische
Journal:  Chemistry       Date:  2019-09-04       Impact factor: 5.236

2.  Conversion of Aldehydes to Branched or Linear Ketones via Regiodivergent Rhodium-Catalyzed Vinyl Bromide Reductive Coupling-Redox Isomerization Mediated by Formate.

Authors:  Robert A Swyka; William G Shuler; Brian J Spinello; Wandi Zhang; Chunling Lan; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-04-18       Impact factor: 15.419

3.  Conversion of Primary Alcohols and Butadiene to Branched Ketones via Merged Transfer Hydrogenative Carbonyl Addition-Redox Isomerization Catalyzed by Rhodium.

Authors:  Brian J Spinello; Jessica Wu; Yoon Cho; Michael J Krische
Journal:  J Am Chem Soc       Date:  2021-08-20       Impact factor: 16.383

4.  Crystal structure of (S)-2-[(3S,8S,9S,10R,13S,14S,17R)-3-hy-droxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetra-deca-hydro-1H-cyclo-penta[a]phenanthren-17-yl]-N-meth-oxy-N-methyl-pro-pan-amide (Fernholz Weinreb amide).

Authors:  Elvar Ørn Viktorsson; Ove Alexander Høgmoen Åstrand; Rasha Sabah Haseeb; Carl Henrik Görbitz; Pål Rongved
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-02-18

5.  Suzuki-type cross-coupling of alkyl trifluoroborates with acid fluoride enabled by NHC/photoredox dual catalysis.

Authors:  Hua Huang; Qing-Song Dai; Hai-Jun Leng; Qing-Zhu Li; Si-Lin Yang; Ying-Mao Tao; Xiang Zhang; Ting Qi; Jun-Long Li
Journal:  Chem Sci       Date:  2022-01-21       Impact factor: 9.825

6.  Direct Addition of Grignard Reagents to Aliphatic Carboxylic Acids Enabled by Bulky turbo-Organomagnesium Anilides.

Authors:  Kilian Colas; A Catarina V D Dos Santos; Stefanie V Kohlhepp; Abraham Mendoza
Journal:  Chemistry       Date:  2022-01-27       Impact factor: 5.020

  6 in total

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