Xylochemicals and where to find them

This article surveys a range of important platform and high value chemicals that may be considered primary and secondary 'xylochemicals'. A summary of identified xylochemical substances and their natural sources is provided in tabular form. In detail, this review is meant to provide useful assistance for the consideration of potential synthetic strategies using xylochemicals, new methodologies and the development of potentially sustainable, xylochemistry-based processes. It should support the transition from petroleum-based approaches and help to move towards more sustainability within the synthetic community. This feasible paradigm shift is demonstrated with the total synthesis of natural …

Glucose as an Eco‐Friendly Reductant in a One‐Pot Synthesis of 2,3‐Dihydroquinazolin‐4(1 H )‐ones

Front Cover: Glucose as an Eco‐Friendly Reductant in a One‐Pot Synthesis of 2,3‐Dihydroquinazolin‐4(1 H )‐ones (Eur. J. Org. Chem. 41/2020)

Front Cover: Visible‐Light‐Induced Cleavage of C−S Bonds in Thioacetals and Thioketals with Iodine as a Photocatalyst (ChemPhotoChem 2/2020)

Programmed Formation of HCN Oligomers through Organosulfur Catalysis

An efficient, inexpensive, and reliable synthesis of diaminomaleonitrile (DAMN, 1) is described starting from readily available acetone cyanohydrin as the source of hydrogen cyanide (HCN). Diaminomaleonitrile (DAMN) is known to be an important intermediate in heterocyclic and medicinal chemistry as well as being a possible precursor for the origin of life's hypothesis within prebiotic chemistry. The mechanism of its formation through organosulfur catalysis has been investigated by electrospray ionization mass spectrometry (ESI-MS) using two newly synthesized cationic "marker" molecules as a tool that allows for sensitive detection. As a result, the proposed mechanism of a thiocyanate-mediat…

‐Aminonitriles: From Sustainable Preparation to Applications in Natural Product Synthesis

Due to their numerous reactivity modes, α-aminonitriles represent versatile and valuable building blocks in organic total synthesis. Since their discovery by Adolph Strecker in 1850, this compound class has seen a wide dissemination in synthetic applications from laboratory to million-ton industrial scale and was extensively used in the syntheses of various classes of natural products. As these compounds provide a multitude of reactivity options, we feel that a broad overview of their multiple reaction modes may reveal less familiar opportunities for successful total synthesis planning. This personal account article will thus focus on α-aminonitriles used as key intermediates in selected na…

Strecker reactions with hexacyanoferrates as non-toxic cyanide sources

The Strecker reaction is the most widely applied three-component reaction. Although highly useful for the preparation of α-amino nitriles, α-amino acids, hydantoins and numerous related compounds, the need for the application of toxic sources of HCN limits its application in both academic and industrial settings. Here, we present a facile protocol for Strecker reactions using a mixture of potassium ferri- and ferrocyanides as a non-toxic substitute.

Visible‐Light‐Induced Cleavage of C−S Bonds in Thioacetals and Thioketals with Iodine as a Photocatalyst