Atroposelective synthesis of axially chiral biaryl compounds

作者：Bringmann G^*; Mortimer AJP; Keller PA; Gresser MJ; Garner J; Breuning M

来源：Angewandte Chemie - International Edition, 2005, 44(34): 5384-5427.

DOI：10.1002/anie.200462661

• asymmetric synthesis
• atropisomerism
• axial chirality
• biaryl compounds
• stereoselectivity

<jats:title>Abstract</jats:title><jats:p>A rotationally hindered and thus stereogenic biaryl axis is the structurally and stereochemically decisive element of a steadily growing number of natural products, chiral auxiliaries, and catalysts. Thus, it is not surprising that significant advances have been made in the asymmetric synthesis of axially chiral biaryl compounds over the past decade. In addition to the classic approach (direct stereoselective aryl–aryl coupling), innovative concepts have been developed in which the asymmetric information is introduced into a preformed, but achiral—that is, symmetric or configurationally labile—biaryl compound, or in which an arylC single bond is stereoselectively transformed into an axis. This Review classifies these strategies according to their underlying concepts and critically evaluates their scope and limitations with reference to selected model reactions and applications. Furthermore, the preconditions required for the existence of axial chirality in biaryl compounds are discussed.</jats:p>

• 出版日期2005