Novel Substrates for Desymmetrization Processes: meso-Benzylic Bisalkynes

Philip Bulman Page und Richard Stephenson describe meso-benzylic bisalkynes as novel substrates for desymmetrization processes.

Convenient Access to meso Benzylic Bisalkynes: P. C. Bulman Page, G. R. Stephenson and co-workers
Synlett 2016, DOI: 10.1055/s-0035-1561318

Desymmetrization reactions play a key role in organic synthesis and represent powerful tools in the arsenal of stereocontrolled reactions. The availability of suitable prostereogenic substrates is central to the desymmetrization strategy. Recently, Professor Philip C. Bulman Page and Professor G. Richard Stephenson from the University of East Anglia (Norwich, UK) and collaborators at Caen (France) and St. Andrews (Scotland, UK) have reported a convenient method for the synthesis of meso bisalkynes and derivatives, which have significant potential as desymmetrization substrates. 

Professor Bulman Page said: “Desymmetrization is a topical and important concept in enantioselective synthesis because it allows several stereogenic centers to be accessed in non-racemic form in a single step from a single prochiral starting material; meso bisalkynes and alkenes have potential as substrates for desymmetrization processes, and we report the preparation of several meso bis(1’-hydroxy-2’-propynyl)benzenes and their derivatives from phthalaldehydes using inexpensive and readily available reagents,” he concluded.