Home
Resources
Publications
Stereoselective Peterson Olefinations From Bench-Stable Reagents and N-phenyl Imines

Stereoselective Peterson Olefinations From Bench-Stable Reagents and N-phenyl Imines

Manas Das, Atul Manvar, Maïwenn Jacolot, Marco Blangetti, Roderick C Jones, Donal F O'Shea

Chemistry. 2015 Jun 8;21(24):8737-40.

PMID: 25761058

Abstract:

The synthesis of bench-stable α,α-bis(trimethylsilyl)toluenes and tris(trimethylsilyl)methane is described and their use in stereoselective Peterson olefinations has been achieved with a wide substrate scope. Product stereoselectivity was poor with carbonyl electrophiles (E/Z ∼1:1 to 4:1) though this was significantly improved by employing the corresponding substituted N-benzylideneaniline (up to 99:1) as an alternative electrophile. The olefination byproduct was identified as N,N-bis(trimethylsilyl)aniline and could be easily separated from product by aqueous acid extraction. Evidence for an autocatalytic cycle has been obtained.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1068695	Tris(trimethylsilyl)methane		1068-69-5	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: