Directing the regioselectivity of the alkylation of pyroglutamate carbamates by formation of a stable counter-ion complex

Authors
Stevens, CV Rammeloo, T De Kimpe, N
Citation
Cv. Stevens et al., Directing the regioselectivity of the alkylation of pyroglutamate carbamates by formation of a stable counter-ion complex, SYNLETT, (10), 2001, pp. 1519-1522
Citations number
16
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
10
Year of publication
2001
Pages
1519 - 1522
Database
ISI
SICI code
0936-5214(200110):10<1519:DTROTA>2.0.ZU;2-2
Abstract
The alkylation of benzyl N-Boc pyroglutamate was carried out using chlorofo rmates in order to introduce an activating group at the 4-position. Deproto nation with three equivalents of LiHMDS followed by alkylation with differe nt electrophiles lead to 2-alkylated pyroglutamates. The directing effect o f the alkylation to the 2-position can be accounted for by the formation of a counterion complex.