Studies on cyclization reactions of 3-amino-2,4-dihydroxybutanoic acid derivatives

被引：9

作者：

Esgulian, Mathieu ^{[1
]}

Belot, Vincent ^{[1
]}

Guillot, Regis ^{[1
]}

Deloisy, Sandrine ^{[1
]}

Aitken, David J. ^{[1
]}

机构：

[1] Univ Paris Saclay, Univ Paris Sud, Organ Synth Grp & Serv Communs CP3A, ICMMO,CNRS, 15 Rue Georges Clemenceau, F-91405 Orsay, France

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 06期

关键词：

BOC PROTECTING GROUP; BETA-AMINO ALCOHOLS; ASYMMETRIC-SYNTHESIS; FORMAL SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; LYXO-PHYTOSPHINGOSINE; BUILDING-BLOCK; ASPARTIC-ACID; ALPHA-AMINO;

D O I：

10.1039/c6ob02759h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A number of cyclic derivatives of 3-amino-2,4-dihydroxybutanoic acid are known in the literature but they are often prepared from other cyclic precursors. This study showed that the title compound too may serve as a convenient substrate for cyclization reactions. Using orthogonally-protected linear derivatives, regioselective cyclizations were performed, leading to original and highly-functionalized gamma-lactones, oxazolidinones, oxazolines and aziridines. In these reactions a key role was played by the C3 nitrogen group function, while the C2 alcohol function showed no propensity for participation in cyclization reactions.

引用

页码：1453 / 1462

页数：10

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