Literature DB >> 27862829

Rhodium-Catalyzed Diastereoselective Cyclization of Allenyl-Sulfonylcarbamates: A Stereodivergent Approach to 1,3-Aminoalcohol Derivatives.

Pierre A Spreider1, Alexander M Haydl1, Marc Heinrich1, Bernhard Breit1.   

Abstract

A diastereoselective and stereodivergent rhodium-catalyzed intramolecular coupling of sulfonylcarbamates with terminal allenes is described and it provides selective access to 1,3-aminoalcohol derivatives, scaffolds found in bioactive compounds. The reaction is compatible with a large range of different functional groups, thus furnishing products with high diastereoselectivities and yields. Moreover, multigram scale reactions, as well as the application of suitable product transformations were demonstrated.
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alcohols; allenes; allylic compounds; rhodium; synthetic methods

Year:  2016        PMID: 27862829     DOI: 10.1002/anie.201609366

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  4 in total

1.  Synthesis of anti-1,3 Amino Alcohol Motifs via Pd(II)/SOX Catalysis with the Capacity for Stereodivergence.

Authors:  Rulin Ma; Jonathon Young; Rossella Promontorio; Friederike M Dannheim; Christopher C Pattillo; M Christina White
Journal:  J Am Chem Soc       Date:  2019-06-05       Impact factor: 15.419

2.  Asymmetric Synthesis of γ-Amino Alcohols by Copper-Catalyzed Hydroamination.

Authors:  Saki Ichikawa; Stephen L Buchwald
Journal:  Org Lett       Date:  2019-10-18       Impact factor: 6.005

3.  Macrolactonization of methyl 15-hydroxypentadecanoate to cyclopentadecanolide using KF-La/γ-Al2O3 catalyst.

Authors:  Haijun Cheng; Chang Yu; Hongyun Wang; Xiongmin Liu; Li Ma; Fang Lai
Journal:  R Soc Open Sci       Date:  2022-09-07       Impact factor: 3.653

4.  Ortho-aryl substituted DPEphos ligands: rhodium complexes featuring C-H anagostic interactions and B-H agostic bonds.

Authors:  James J Race; Arron L Burnage; Timothy M Boyd; Alex Heyam; Antonio J Martínez-Martínez; Stuart A Macgregor; Andrew S Weller
Journal:  Chem Sci       Date:  2021-05-25       Impact factor: 9.825

  4 in total

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