Organic Chemistry Seminar: Rapid, Modular and Stereodivergent Synthesis of Acyclic 1,4-Stereocenters: Experiment Design, Scope and Mechanistic Insight

Dr. David Pierrot, Technion/Arkadi

15 December 2019, 16:00 
Shenkar Building, Holcblat Hall 007 
Organic Chemistry Seminar

Abstract:

The preparation of acyclic molecules bearing multiple elements of complexity (unsaturations, centers of chirality) has been a great challenge for synthetic chemists when these elements are located in a close vicinity.  While many methods enable the enantioselective preparation of specific templates,  stereodiversity can mostly be accessed through long linear sequences. Recent stereodivergent preparations of 1,2-contiguous stereocenters received great interest from the community. In order to pursue the chemical space’s exploration,  more rapid and efficient preparations of any stereoisomer of a given stereofamily are required.

 

Owing to a specific substrate design (Scheme 1), we could access acyclic 1,4-stereocenters in a stereodivergent manner through two different approaches. A palladium-catalyzed remote functionalization approach leads to the 1,2,5-stereocenter family 2.  A metal-free catalytic diboration strategy afforded the preparation of 1,4-stereocenter family 3 containing an allylic boronic ester functional group.  Both methods are versatile and enable the preparation of both tertiary or quaternary stereocenters in a stereodivergent approach. 

 

 

 

  1. D. Pierrot, I. Marek, Angew. Chem. Int. Ed. 2019, 58, 2-16. 

  2. S. Krautwald, D. Sarlah, M. A. Schafroth, E. M. Carreira, Science 2013, 340, 1065.

  3. D. Kaldre, I. Klose, N. Maulide, Science 2018, 361, 664.

  4. J.-L. Reymond, Acc. Chem. Res. 2015, 48, 722.

  5. J. Bruffaerts, D. Pierrot, I. Marek, Nature Chem. 2018, 10, 1164.

  6. Unpublished results

 

 

 

Event Organizer: Dr. Roman Dobrovetsky

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