Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 60, No. 8, 2003, pp.1843-1854
Published online, 7th July, 2003
DOI: 10.3987/COM-03-9806
Stereoselective Conjugate Addition of Metallated 2-Methylpyridine to Functionalized α,β-Unsaturated Carbonyl Compounds

Francisco Sánchez-Sancho and Bernardo Herradón*

*Instituto de Química Orgánica General, C. S. I. C., Calle Juan de Cierva, 3, 28006 Madrid, Spain

Abstract

The reaction of bis-(2-pyridylmethyl)cyanocuprate (3) with a variety of α,β-unsaturated carbonyl compounds is reported. It has been found that while the reaction with enone goes through a 1,2-addition path, the outcome of the reaction with α,β-unsaturated esters depends on the structure of the electrophile, giving the conjugate addition product with γ-hetero-substituted α,β-unsaturated esters. On the other hand, the reaction of 3 with oxygenated butenolides is stereoselective, affording the 1,4-addition product.