(2<em>R</em>,3<em>R</em>)-1,4-Dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol: Valuable reagent in the asymmetric synthesis of organoboronates

Berg, C. Annette; Eichenauer, Nils C.; Pietruszka, Jörg

doi:10.1351/PAC-CON-12-03-04

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Pure Appl. Chem., 2012, Vol. 84, No. 11, pp. 2339-2416

http://dx.doi.org/10.1351/PAC-CON-12-03-04

Published online 2012-09-10

(2R,3R)-1,4-Dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol: Valuable reagent in the asymmetric synthesis of organoboronates

C. Annette Berg, Nils C. Eichenauer and Jörg Pietruszka*

Institut für Bioorganische Chemie der Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich, Stetternicher Forst, Geb.15.8, 52426 Jülich, Germany

Abstract: Tartrate-derived (2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol has found diverse applications in asymmetric organic synthesis. Among these, its utilization as a protecting group for boronic acids has been investigated extensively. Besides being extraordinarily stable and thus allowing a plethora of transformations, it enables access to various diastereo- and enantiomerically pure organoboron reagents and versatile intermediates in asymmetric synthesis.