Methyl 2-(Benzyloxycarbonylamino)-2-cyclopropylideneacetate: A Versatile Building Block for Cyclopropyl-Containing Amino Acids

被引：8

作者：

Limbach, Michael ^{[1
]}

Lygin, Alexander ^{[1
]}

Es-Sayed, Mazen ^{[2
]}

de Meijere, Armin ^{[1
]}

机构：

[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany

[2] Bayer CropSci AG, D-40789 Monheim, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 09期

关键词：

Cyclopropanes; Amino acids; Michael addition; Peptidomimetics; Molecular diversity; OPTICALLY-ACTIVE OXAZOLIDINONES; ORGANIC-SYNTHESIS; NATURAL OCCURRENCE; MICHAEL DONORS; DERIVATIVES; REACTIVITY; OLEFINS; STRAIN;

D O I：

10.1002/ejoc.200800817

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methyl 2-(benzyloxycarbonylamino)-2-cyclopropylideneacetate (2) was prepared in nine steps starting from L-serine in an overall yield of 24 %. It has been demonstrated to be reasonably reactive in Michael additions of various nucleophiles (6 examples, 75-98%) yields) as well as Diels-Alder reactions, both leading to new cyclopropyl-containing amino acids in protected form. An application of 2 in the synthesis of methyl 4-tert-butoxycarbonylmethyl-5-oxo-4,7-diazaspiro-[2.5]octane-8-carboxylate (15), a precursor for geometrically constrained bicyclic peptidomimetics of type 16, has also been proved. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：1357 / 1364

页数：8

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