Citation
C. Kashima et al., DIASTEREOSELECTIVE ALPHA-ALKYLATION OF 2-ACYL-3-PHENYL-L-MENTHOPYRAZOLES, Journal of organic chemistry, 59(25), 1994, pp. 7821-7824
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00223263
Volume
59
Issue
25
Year of publication
1994
Pages
7821 - 7824
Database
ISI
SICI code
0022-3263(1994)59:25<7821:DAO2>2.0.ZU;2-9
Abstract
N-Acylpyrazoles were alpha-alkylated in good yields by the treatment w
ith alkyl halides after metalation with LDA or LiHMDS, In the case of
chiral N-acylpyrazoles, e.g., 2-acyl-3-phenyl-l-menthopyrazoles (4), t
he alpha-alkylation was highly diastereoselective. The subsequent alph
a-alkylation products could be converted into esters in good yield in
the presence of BF3.OEt(2) without the loss of the optical purity.