𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis of γ-Hydroxy-α,β-unsaturated Esters and Nitriles from Chiral Cyanohydrins

✍ Scribed by Jan Marcus; Pauline J. van Meurs; Adrianus M.C.H. van den Nieuwendijk; Mathieu Porchet; Johannes Brussee; Arne van der Gen

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
145 KB
Volume
56
Category
Article
ISSN
0040-4020

No coin nor oath required. For personal study only.

✦ Synopsis

The Horner-Wittig reaction of cyanomethyl-and carbethoxymethyl diphenylphosphine oxides with a range of O-protected chiral a-hydroxy aldehydes is described. The a-hydroxy aldehydes were prepared with high enantiomeric purity from chiral O-protected cyanohydrins. The g-hydroxy-a,b-unsaturated compounds formed were isolated in high enantiomeric purity and excellent yield. In all cases complete E-selectivity was observed.

📜 SIMILAR VOLUMES

Diastereoselective and Enantiospecific S
Diastereoselective and Enantiospecific Synthesis of γ-Substituted α,β-Unsaturated Nitriles from O-Protected Allylic Cyanohydrins.
✍ Alejandro Baeza; Jesus Casas; Carmen Najera; Jose M. Sansano 📂 Article 📅 2006 🏛 John Wiley and Sons ⚖ 65 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Palladium-catalyzed regioselective react
Palladium-catalyzed regioselective reactions of α-acetoxy-β,γ-unsaturated nitriles and γ-acetoxy-α,β-unsaturated ester with nucleophiles
✍ Jiro Tsuji; Hiroaki Ueno; Yuichi Kobayashi; Hiroshi Okumoto 📂 Article 📅 1981 🏛 Elsevier Science 🌐 French ⚖ 120 KB

e-Acetoxy-8,y-unsaturated nitriles react at room temperature with malonates and acetoacetates in the presence of palladium-phosphine complexes as a catalyst to give y-substituted a,8-unsaturated nitriles selectively. Also yacetoxy-a,8-unsaturated ester was attacked at y-position by malonate.

Additive pummerer reactions of vinylic s
Additive pummerer reactions of vinylic sulphoxides. Synthesis of γ-hydroxy-α,β-unsaturated esters and α-hydroxyketones
✍ Donald Craig; Kevin Daniels; A.Roderick MacKenzie 📂 Article 📅 1990 🏛 Elsevier Science 🌐 French ⚖ 285 KB

## Reaction of a,&unsaturated sulphoxides with trtfluoroacetic anhydri& gives a,j+bis(trifhwroacetoxy)thioethers in near-quantitative yields. Subsequent basic methanolysis gives monomeric and dimeric a-hydroxyaldehydes or ahydroxyketones, &pending on the nature of the 8-R group. The former undergo W