Citation
S. Maas et al., Conjugate addition of dialkylaluminum chlorides to alkylidenemalonic acid derivatives, SYNTHESIS-S, (10), 1999, pp. 1792-1798
Citations number
33
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881
→ ACNP
Issue
10
Year of publication
1999
Pages
1792 - 1798
Database
ISI
SICI code
0039-7881(199910):10<1792:CAODCT>2.0.ZU;2-3
Abstract
Complete regioselectivity is achieved in conjugate addition reactions of di
alkylaluminum chlorides with alkylidenemalonic esters, alkylidenecyanoaceta
tes, and alkylidenemalonodinitrile to give beta-branched carboxylic acid de
rivatives. Sterically demanding products containing quaternary carbon atoms
are obtained in good yields. In the case of diethylaluminum chloride, acco
mpanying reductions of the substrates can be suppressed by application of b
oron trifluoride as an assisting Lewis acid.