Organoboron Chemistry

In synthetic organic chemistry, organoboron reagents have gained an important role as versatile and reliable building blocks for C-C and C-heteroatom bond-forming reactions. At present, the diversity of methods for preparation of organoboronic acids and esters as well as the variety of synthetic applications is steadily increasing.

In our working group’s research on organoboron chemistry, we focus on the development of methods for the efficient and selective synthesis of diastereo- and enantiomerically pure organoboron reagents. These reagents are versatile intermediates in asymmetric synthesis. Therein, a key feature is the utilization of tartrate-derived diol 1 as boronic acid protective group, providing highly stable boronic esters. Cyclopropylboronic esters and allylic boronates are compounds of special interest to us. In the preparation of a variety of enantiomerically pure cyclopropylboronic esters, it has been found that chiral auxiliary 1 does not only induce selectivity but allows a wide number of transformations in the side-chain “R” in the presence of the boron group by providing stability to the molecule. Thus, useful bifunctional buildings blocks are provided for natural product and drug synthesis.

Selected Publications

Yvonne Gehrke, Christina Anette Berg, Roza Vahabi, Jörg Pietruszka, Eur. J. Org. Chem. 2016, 2413-2420; "Synthesis of New Alkenylboronic Esters - An Alternative Route towards Trisubstituted Homoallylic Alcohols"

Marcus Brauns, Frédéric Muller, Daniel Gülden, Dietrich Böse, Wolfgang Frey, Martin Breugst, Jörg Pietruszka, Angew. Chem. Int. Ed. 2016, 55, 1548-1552; "Enantioselective Catalysts for the Synthesis of a-Substituted Allylboronates - An Accelerated Approach towards Isomerically Pure Homoallylic Alcohols"

Dietrich Böse, Wolfgang Frey, Jörg Pietruszka, Synthesis 2014, 46, 2524-2532; "The ‘Mikami’-Catalyst in Enantioselective Diels–Alder Reactions of Juglone-Based Dienophiles with Different 1-Oxygenated Dienes: An Investigation on the Substitution Pattern Dependent Regioselectivity"

Roza Vahabi, Wolfgang Frey, Jörg Pietruszka, J Org Chem. 2013, 78(22), 11549-11559; "Synthesis of highly-substituted enantiomerically pure allylboronic esters - investigation of their stereoselective addition to aldehydes"

Responsible for the content: E-MailJörg Pietruszka