𝔖 Bobbio Scriptorium
✦   LIBER   ✦

The cerium mediated conversion of esters to allylsilanes

✍ Scribed by B.A. Narayanan; W.H. Bunnelle

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
246 KB
Volume
28
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

Reaction of esters with the reagent prepared from CeCl and TMSCH MgCl 6 in THF, followed by deoxysilylation on silica gel, eff&ts efficient conve sion to allylsilanes. Methyl 1-adamantane carboxylate, a sterically hindered ester, does not react under these conditions. Allylsilanes are exceptionally versatile compounds with well-established utility in organic synthesis.' Thus, general methods for the development of the allylsilane functionality, particularly those applicable to complex molecules, are quite valuable. Consequently, there has been much recent interest in carboxylic acid derivatives as functional precursors for allylsilanes. 2,3

The transformation is conceptually staightforward: twofold a.ddition of a trimethylsilymethyl-metal

πŸ“œ SIMILAR VOLUMES

The cerium (III) mediated reaction of tr
The cerium (III) mediated reaction of trimethylsilylmethyl magnesium chloride with esters and lactones: The efficient synthesis of some functionalised allylsilanes of use in annulation reactions
✍ Thomas V. Lee; Julia A. Channon; Carmel Cregg; John R. Porter; Frances S. Roden; πŸ“‚ Article πŸ“… 1989 πŸ› Elsevier Science 🌐 French βš– 714 KB

## The use of cerium (Ill) chloride alters the chemoselectivity of the reaction of trimethylsilybnethyl magnesium chloride with ester-acetals and also greatly improves the e#iciency of reaction with lactones. In addition it gives improved preparations of the uqtiil intermediates ( ), ( ), ( ),(

IBX-Mediated Conversion of Primary Alcoh
IBX-Mediated Conversion of Primary Alcohols and Aldehydes to N-Hydroxysuccinimide Esters
✍ Agnes Schulze; Athanassios Giannis πŸ“‚ Article πŸ“… 2004 πŸ› John Wiley and Sons 🌐 English βš– 117 KB πŸ‘ 2 views

## Abstract Recently, the use of the hypervalent iodine reagent 1‐hydroxy‐1,2‐benziodoxol‐3(1__H__)‐one 1‐oxide (IBX) for the oxidation of primary alcohols and aldehydes to carboxylic acids was described. During the synthesis of these carboxylic acids the corresponding __N__‐hydroxysuccinimide este

The conversion of steroidal lactones to
The conversion of steroidal lactones to ortho esters
✍ R.A. LeMahieu; R.W. Kierstead πŸ“‚ Article πŸ“… 1970 πŸ› Elsevier Science 🌐 French βš– 85 KB

The conversion of lactones to ortho esters has been accomplished by treatment with epoxides in the presence of boron trifluoride (1) or with triethyloxonium fluoroborate followed by sodium et&oxide. (2) We have recently found that ketalization of steroidal ketones containing a lactone group also res