The biosynthesis of the cyanogenic glucosides, linamarin and prunasin, was investigated in linen-flax, peach and cherry-laurel shoots. It was shown that related 2-oximino acids, aldoximes, nitriles and 2-hydroxynitriles were generally good precursors of the aglycone moiety. Studies with double-labelled compounds confirmed the retention of the oximino nitrogen atom from 2-oximinoisovaleric acid ...

In this work, we describe the one-pot synthesis of α-amino nitrile units by concomitant addition alkyl (or aryl) Grignard reagents and TMS cyanide through alkylative Strecker cyanation from readily available formamides. The reaction is broad in scope conditions are mild, inexpensive, easy to set-up, providing numerous nitriles good yields (34 examples, 41–94 % yield).

The cover art illustrates the phase-transfer catalysis effective for asymmetric Strecker reaction of ketoimines with potassium cyanide under solid-liquid biphasic conditions. Chiral 1,2,3-triazolium ion featuring prominent hydrogen-bond donating and anion-binding capabilities allows establishment a highly efficient enantioselective process preparation sterically congested chiral α-amino nitrile...

We report the first catalytic asymmetric cyanation of N-Boc ketoimines, which enables highly enantioselective synthesis of oxindole based α-amino nitriles. An unprecedented tandem aza-Wittig/Strecker reaction is also developed, emerging as a promising strategy for the catalytic asymmetric cyanation of ketoimines formed in situ from achiral ketones.

A tin-catalyzed reaction of α-hydroxy ketones with 1,1-dicyanoalkenes produced 2-amino-4,5-dihydrofuran-3-nitriles. In the catalytic reaction, tin enolates were generated from α-hydroxy ketones as active catalytic species. The highly basic ability of the Sn-O bonds played an important role in the reactions. This tin-catalyzed reaction was highly atom-economical and required no other metal reage...

A simple, rapid and efficient practical method for one-pot synthesis of α-amino nitriles has been achieved by a threecomponent condensation of carbonyl compounds, amines and trimethylsilyl cyanide in the presence of p-toluenesulfonic acid (p-TsOH) as a catalyst at ambient temperature. Operational simplicity, economic consideration, high yield, short reaction time and low toxicity are the key fe...

To All(oc) involved: A palladium-catalyzed formal 5-endo-trig heteroannulation of enones generated in situ from amino acid derived β-keto nitriles has been realized (see scheme; Alloc=allyl carbamate). The reaction proceeds with allyl-group transfer from the carbamate protecting group to generate two new contiguous stereocenters, including one quaternary center, with high selectivity.