Efficient 1,5-chirality transfer in palladium-catalyzed allylic alkylations of chelated amino acid ester enolates

被引：53

作者：

Kazmaier, U ^{[1
]}

Lindner, T ^{[1
]}

机构：

[1] Univ Saarland, Inst Organ Chem, D-66123 Saarbrucken, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 21期

关键词：

allylation; amino acids; chelates; enolates; palladium;

D O I：

10.1002/anie.200500095

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Neither the olefin geometry nor the configuration of secondary allylic substrates in palladium-catalyzed allylic alkylations of chelated enolates has an influence on the newly formed stereogenic center of the amino acid (see scheme, TBDPS = tert- butyldiphenylsilyl, Tfa = trifluoroacetyl). This is controlled exclusively by the protecting group on the chiral center. Therefore, the choice of the protecting group on the allylic alcohol can lead to either of the diastereomeric amino acids in a highly stereoselective fashion. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3303 / 3306

页数：4

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