Diastereotopos-differentiating allylic alkylation as a key step in the synthesis of gamma-glutamyl boletine.
A straightforward approach towards gamma-glutamyl boletine is described, based on a diastereotopos-differentiating allylic alkylation of chelated amino acid ester enolates. Independent of the configuration of the leaving group in the allylic substrate, the allylation product is obtained as a single stereoisomer. Its configuration is solely controlled by the stereogenic center adjacent to the pi-allyl complex formed.
Gawas
Dnyaneshwar
D
Institut für Organische Chemie, Universität des Saarlandes, D-66123 Saarbrücken, Germany.
Kazmaier
Uli
U