סמינר בכימיה אורגנית: Rapid, Modular and Stereodivergent Synthesis of Acyclic 1,4-Stereocenters: Experiment Design, Scope and Mechanistic Insight
Dr. David Pierrot, Technion/Arkadi
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.
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מארגן האירוע: ד"ר רומן דוברובצקי