Diastereotopos-differentiating allylic alkylation as a key step in the synthesis of γ-glutamyl boletine

被引：8
作者：
Gawas, Dnyaneshwar [1 ]
Kazmaier, Uli [1 ]
机构：
[1] Univ Saarland, Inst Organ Chem, D-66123 Saarbrucken, Germany
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 02期
关键词：
AMINO-ACID ESTERS; EFFICIENT NUCLEOPHILES; PALLADIUM; ISOMERIZATION; SUBSTITUTIONS; ENOLATE;
D O I：
10.1039/b917589j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
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页码：457 / 462
页数：6
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