Enamine catalysis in the synthesis of chiral structural analogues of gem-bisphosphonates known to be biologically active

被引：28
作者：
Barros, Maria Teresa [1 ]
Phillips, Ana Maria Faisca [1 ]
机构：
[1] Univ Nova Lisboa, Fac Ciencias & Tecnol, CQFB REQUIMTE, Dept Chem, P-2829516 Caparica, Portugal
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 15期
关键词：
gem-bisphosphonates; organocatalysis; asymmetric synthesis; Michael addition; ketones;
D O I：
10.1002/ejoc.200800170
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of chiral gamma-keto bisphosphonates is described. Michael addition of cyclic ketones to vinyl gem-bisphosphonate catalyzed by 0.1 mol equiv. (S)-(+)-1-(2-pyrrolidinyl)-pyrrolidine and benzoic acid gave the products in yields of up to 86%, dr (cis/trans) > 1:99 and ee of up to 99 %. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
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页码：2525 / 2529
页数：5
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