𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Electrooxidative rearrangement of tosylamino group: Facile synthesis of α-amino aldehydes from primary amines

✍ Scribed by Tatsuya Shono; Yoshihiro Matsumura; Susumu Katoh; Kenji Inoue; Yonetatsu Matsumoto

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
224 KB
Volume
27
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

Anodic oxidation of primary N-tosylamines in methanol containing halide ion qave cl-(N-tosvlamino) aldehvde dimethvl acetals. svntheticallv useful intera-Amino though their ol-tosylamino mediates equiialent to a-amjno aldehybes. . " " aldehydes are versatile intermediates in the synthesis of nitrogen-heterocycles,' synthesis is not always easy. 3 We wish to report a facile synthetic method of acetals 2, equivalent to a-amino aldehydes, from primary N-tosylamines 1 utilizing anodic oxidation. This novel method is interesting from not only a synthetic but also a mechanistic viewpoint, since the anodic oxidation involves a hitherto unknown oxidative rearrangement of tosylamino group as shown in eq. 1. RkNH-Ts -4e -(I) dMe

📜 SIMILAR VOLUMES

A facile synthesis of primary amines fro
A facile synthesis of primary amines from carboxylic acids by the curtius rearrangement
✍ Todd L. Capson; C.Dale Poulter 📂 Article 📅 1984 🏛 Elsevier Science 🌐 French ⚖ 197 KB

Ab4tic.Z . 2-Trimethylsilylethanol was used to trap isocyanates produced by the Curtius rearrangement of acyl azides and the resulting trimethylsilylethyl carbamates were readily cleaved with tetra-n-butylammonium fluoride to liberate the primary amines.

ChemInform Abstract: Catalytic Asymmetri
ChemInform Abstract: Catalytic Asymmetric Strecker Synthesis. Preparation of Enantiomerically Pure α-Amino Acid Derivatives from Aldimines and Tributyltin Cyanide or Achiral Aldehydes, Amines, and Hydrogen Cyanide Using a Chiral Zirconium Catalyst.
✍ Haruro Ishitani; Susumu Komiyama; Yoshiki Hasegawa; Shu Kobayashi 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 43 KB 👁 2 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

Three-component or four-component coupli
Three-component or four-component coupling reactions leading to δ-lactams. Facile synthesis of γ-acyl-δ-lactams from silyl enolates, α,β-unsaturated thioesters, and imines or amines and aldehydes via tandem Michael-imino aldol reactions
✍ Shū Kobayashi; Ryo Akiyama; Mitsuhiro Moriwaki 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 230 KB

Various ?~acyl-&lactam derivatives were prepared on the basis of threecomponent (silyl enolates, a, fl-unsaturated thioesters, and imines) or four-component (silyl enolates, a,~-unsaturated thioesters, amines, and aldehydes) coupling reactions via Lewis acid-catalyzed tandem Michael-imino aldol reac