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Enantio- and Diastereoselective Suzuki-Miyaura Coupling with Racemic Bicycles

preprint
submitted on 23.05.2019 and posted on 24.05.2019 by Friedrich Wieland Goetzke, Mike Mortimore, Stephen P. Fletcher
Herein we describe a rhodium-catalyzed enantio- and diastereoselective Suzuki-Miyaura cross-coupling between racemic fused bicyclic allylic chlorides and boronic acids. The highly stereoselective transformation allows for the coupling of aryl-, heteroaryl- and vinyl boronic acids and gives access to functionalized bicyclic cyclopentenes which can be converted to other five-membered ring scaffolds with up to five contiguous stereocenters. Preliminary mechanistic studies suggest that these reactions occur with overall retention of the relative stereochemistry and is enantioconvergent for pseudo-symmetric allylic chloride starting materials. In addition, a bicyclic allylic chloride starting material without pseudo-symmetry undergoes a highly enantioselective regiodivergent reaction.

Funding

UK Engineering and Physical Sciences Research Council (EP/N022246/1)

AFR PhD Grant, National Research Fund, Luxembourg

EPSRC Doctoral Training Partnership (DTP) studentship (EP/N509711/1

Vertex Pharmaceuticals

History

Email Address of Submitting Author

wieland.goetzke@chem.ox.ac.uk

Institution

University of Oxford

Country

United Kingdom

ORCID For Submitting Author

0000-0002-8688-5609

Declaration of Conflict of Interest

Oxford University Innovation has filed a patent application (PCT/GB2016/051612) with S.P.F. named as an inventor. F.W.G.and M.M. declare no competing financial interests.

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