Ring Expansion of Cyclic β-Amino Alcohols Induced by Diethylaminosulfur Trifluoride: Synthesis of Cyclic Amines with a Tertiary Fluorine at C3

被引：42

作者：

Anxionnat, Bruno ^{[1
]}

Robert, Benoit ^{[2
]}

George, Pascal ^{[3
]}

Ricci, Gino ^{[4
]}

Perrin, Marc-Antoine ^{[2
]}

Pardo, Domingo Gomez ^{[1
]}

Cossy, Janine ^{[1
]}

机构：

[1] CNRS, ESPCI ParisTech, Chim Organ Lab, F-75231 Paris 05, France

[2] Sanofi, LGCR Dept 13, Res & Dev, F-94403 Vitry Sur Seine, France

[3] Sanofi, Res & Dev, F-91385 Chilly Mazarin, France

[4] Sanofi, Proc Dev, F-04210 Sisteron, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 14期

关键词：

SUBSTITUTED; 3-FLUOROPIPERIDINES; ORGANOFLUORINE CHEMISTRY; ASYMMETRIC CYCLIZATION; KETO-ESTERS; MEMORY; CHIRALITY; ALKYLATION; PROLINOLS; ACIDS;

D O I：

10.1021/jo300887u

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

As the replacement of a hydrogen atom by a fluorine atom in a compound can have an important impact on its biological properties, the development of methods allowing the introduction of a fluorine atom is of great importance. The scope and limitations of the ring expansion of cyclic 2-hydroxymethyl amines induced by diethylaminosulfur trifluoride (DAST) to produce cyclic beta-fluoro amines was studied as well as the enantioselectivity of the process.

引用

页码：6087 / 6099

页数：13

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