Reductive Amination Routes in the Synthesis of Piperidine IminoSugars

被引：21

作者：

Clemente, Francesca ^{[1
]}

Matassini, Camilla ^{[1
]}

Cardona, Francesca ^{[1
,2
]}

机构：

[1] Univ Firenze, Dipartimento Chim Ugo Schiff, Via Lastruccia 3-13, I-50019 Sesto Fiorentino, FI, Italy

[2] Univ Bari, Consorzio Interuniv Nazl Ric Metodol & Proc Innov, I-70125 Bari, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 29期

关键词：

Reductive amination; Iminosugars; Carbohydrates; Polyhydroxylated piperidines; Glycosidase inhibitors; Pharmacological chaperones; N-ALKYLATED DERIVATIVES; PHARMACOLOGICAL CHAPERONES; BIOLOGICAL EVALUATION; NUCLEOPHILIC ADDITIONS; D-GLUCOSE; D-FRUCTOSE-6-PHOSPHATE ALDOLASE; STEREOSELECTIVE-SYNTHESIS; GLYCOSIDASE INHIBITORS; SELECTIVE INHIBITORS; ASYMMETRIC-SYNTHESIS;

D O I：

10.1002/ejoc.201901840

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reductive amination (RA) reaction plays a pivotal role in the synthesis of new C-N bonds, due to the availability of many different and low-cost reagents and their operational simplicity. The introduction in a compound of a nitrogen-containing moiety that can be reduced to an amine in the reaction medium allows to perform cascade reactions which further expand this method. The application of the intramolecular version of the RA to carbohydrates allows the synthesis of polyhydroxypiperidine iminosugars, which are among the most challenging and fascinating glycomimetics for a synthetic chemist. This minireview focuses on the use of RA and of the double reductive amination (DRA) reaction in the key ring-closing step en route to the synthesis of these compounds.

引用

页码：4447 / 4462

页数：16

共 104 条

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