EFFICIENT SYNTHESIS OF METHYL 2-(TERT-BUTYL)ACRYLATE AND ANALOGOUS ESTERS

Authors
XU LH KUNDIG EP
Citation
Lh. Xu et Ep. Kundig, EFFICIENT SYNTHESIS OF METHYL 2-(TERT-BUTYL)ACRYLATE AND ANALOGOUS ESTERS, Helvetica Chimica Acta, 77(6), 1994, pp. 1480-1484
Citations number
22
Categorie Soggetti
Chemistry
Journal title
Helvetica Chimica Acta → ACNP
ISSN journal
0018019X
Volume
77
Issue
6
Year of publication
1994
Pages
1480 - 1484
Database
ISI
SICI code
0018-019X(1994)77:6<1480:ESOM2A>2.0.ZU;2-8
Abstract
The title products are prepared via an efficient three-step synthesis which involves hydroalumination of methyl propiolate and Lewis-acid-pr omoted reaction with acetone in the presence of BF3 followed by two hi ghly selective S(N)2' reactions. The key step is the reaction of 2-(ch loromethyl)acrylates with R(2)CuLi/ZnCl2 reagents which takes place wi th complete allylic rearrangement.