采用哌啶酸酯支架的立体化学和骨架多样性。

Stereochemical and skeletal diversity employing pipecolate ester scaffolds.

作者信息

Chen Yu, Porco John A, Panek James S

机构信息

Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Metcalf Center for Science and Engineering, 590 Commonwealth Avenue, Boston University, Boston, Massachusetts 02215, USA.

出版信息

Org Lett. 2007 Apr 12;9(8):1529-32. doi: 10.1021/ol070321g. Epub 2007 Mar 17.

DOI:10.1021/ol070321g

PMID:17367153

Abstract

[structure: see text] The stereocontrolled synthesis of pyridooxazinones by Mg(OTf)2-promoted epoxide ring-opening with use of chiral pipecolates as nucleophiles is described. Pyridooxazinone products derived from azido-epoxides can be further rearranged to seven-membered pyridodiazepinones by azide reduction. The sequence of functional group interconversions generates diversity through topological and stereochemical variation.

摘要

[结构：见正文] 描述了通过使用手性哌啶甲酸盐作为亲核试剂，由Mg(OTf)₂促进环氧化物开环进行吡啶并恶嗪酮的立体控制合成。由叠氮基环氧化物衍生的吡啶并恶嗪酮产物可通过叠氮基还原进一步重排为七元吡啶并二氮杂卓酮。官能团相互转化的序列通过拓扑和立体化学变化产生多样性。