Synthesis of β-Hydroxy Nitriles via Indium-Induced Coupling of Bromoacetonitrile with Carbonyl Compounds
- 1 April 1994
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 67 (4) , 1126-1129
- https://doi.org/10.1246/bcsj.67.1126
Abstract
The organoindium reagent, derived from indium metal and bromoacetonitrile, reacted with carbonyl compounds in the presence of chlorotrimethylsilane to give, after hydrolysis, β-hydroxy nitriles. The coupling proceeded with high chemoselectivity, though the diastereoselectivity was low.This publication has 14 references indexed in Scilit:
- Synthesis of Homoallylamines by the Addition of Allylic Indium Reagents to Azomethines and NitrilesBulletin of the Chemical Society of Japan, 1993
- Allylation of Carbonyl Compounds with Catalytic Amount of IndiumBulletin of the Chemical Society of Japan, 1992
- Carboindation of alkynols. A facile synthesis of yomogi alcoholTetrahedron Letters, 1992
- Allylation of quinones by allylic indium reagentsJournal of Organometallic Chemistry, 1991
- Preparation and some reactions of allylic indium reagentsThe Journal of Organic Chemistry, 1991
- Indium-Induced Reaction of Phenacyl Iodide. Deiodinative Dimerization to β,γ-Epoxy Ketone and Aldol Condensation with AldehydesBulletin of the Chemical Society of Japan, 1991
- Indium-induced allylation of acid anhydrides: A facile synthesis of allylated butenolides and phthalidesTetrahedron Letters, 1989
- A Barbier allylation and a Reformatsky reaction of carbonyl compounds mediated by indium(I) iodideJournal of Organometallic Chemistry, 1989
- Synthesis of β-Hydroxyesters by Reformatsky Reaction Using Indium MetalSynthetic Communications, 1988
- Indium in organic synthesis: indium-mediated allylation of carbonyl compoundsThe Journal of Organic Chemistry, 1988